Organocatalytic asymmetric direct vinylogous Michael ... · Organocatalytic asymmetric direct...

54
Organocatalytic asymmetric direct vinylogous Michael addition of α,β- unsaturated γ-butyrolactam to nitroolefins Abhijnan Ray Choudhury and Santanu Mukherjee* Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, INDIA [email protected] SUPPORTING INFORMATION: PART B Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2012

Transcript of Organocatalytic asymmetric direct vinylogous Michael ... · Organocatalytic asymmetric direct...

Page 1: Organocatalytic asymmetric direct vinylogous Michael ... · Organocatalytic asymmetric direct vinylogous Michael addition of ... Department of Organic Chemistry, ... SI-Part-B, Page

Organocatalytic asymmetric direct vinylogous Michael addition of α,β- unsaturated γ-butyrolactam to nitroolefins

Abhijnan Ray Choudhury and Santanu Mukherjee*

Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, INDIA

[email protected]

SUPPORTING INFORMATION: PART B 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-2

 

10 9 8 7 6 5 4 3 2 1 0 ppm

4.00

14.

006

6.09

06.

095

6.09

8

7.10

87.

112

8.17

4

2.11

0

0.92

9

0.94

9

1.00

0

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

49.0

89

76.8

4577

.164

77.4

82

127.

592

146.

099

175.

679

 

NH

O

NH

O

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 0 ppm

1.53

0

4.32

7

6.12

46.

128

6.13

56.

140

7.16

47.

169

7.17

57.

180

9.32

5

2.04

9

0.96

4

1.00

0

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.0

04

51.5

72

76.6

8677

.004

77.3

2282

.894

127.

827

145.

114

149.

473

169.

094

N O

Boc1

N O

Boc1

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10 9 8 7 6 5 4 3 2 1 0 ppm

0.87

40.

887

1.27

01.

289

1.30

61.

351

1.37

61.

693

2.03

72.

244

2.27

12.

300

2.34

12.

669

2.83

82.

865

2.89

23.

050

3.39

63.

414

3.79

73.

815

4.98

15.

006

5.04

95.

370

6.01

36.

058

6.07

8

7.03

87.

301

7.42

57.

569

7.58

07.

886

7.90

9

8.61

08.

620

1.19

6

2.12

3

1.05

1

0.90

0

1.78

6

0.83

30.

998

0.87

7

0.81

3

1.78

8

1.89

2

2.03

10.

885

1.12

51.

026

0.91

5

1.00

0

 

N

HN

OH

OH

III

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10 9 8 7 6 5 4 3 2 1 0 ppm

1.00

01.

017

1.12

41.

248

1.48

01.

504

1.52

41.

754

2.00

72.

031

2.03

62.

043

2.06

32.

079

2.09

52.

220

2.24

12.

754

2.76

42.

785

2.87

52.

900

2.90

82.

933

3.04

63.

056

3.34

73.

366

3.71

03.

726

5.01

95.

027

5.05

75.

608

5.61

75.

998

6.02

37.

137

7.14

37.

265

7.27

17.

277

7.29

47.

300

7.49

97.

511

7.91

47.

937

8.58

08.

591

5.86

21.

016

1.27

12.

214

1.02

42.

139

0.94

8

1.17

82.

053

1.03

21.

043

1.93

2

1.91

3

0.91

4

0.94

2

1.06

90.

895

1.00

7

1.01

1

1.00

0

200 180 160 140 120 100 80 60 40 20 0 ppm

19.2

2821

.063

26.2

2228

.171

39.8

86

49.5

4150

.088

59.6

2571

.667

74.5

8676

.682

77.0

0077

.318

101.

776

114.

600

118.

412

121.

850

121.

855

126.

545

131.

335

140.

389

143.

944

147.

311

147.

408

157.

284

 

N

HN

OH

OIV

N

HN

OH

OIV

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 0 ppm

0.82

20.

840

0.85

80.

963

0.97

60.

996

1.01

81.

029

1.34

01.

359

1.37

71.

408

1.42

51.

642

1.93

61.

961

1.99

12.

664

2.67

42.

696

2.71

72.

787

2.81

42.

838

2.84

62.

871

2.92

82.

943

2.94

82.

964

3.09

23.

111

3.12

33.

143

3.76

25.

264

5.57

85.

585

7.12

17.

187

7.19

27.

210

7.21

57.

260

7.47

27.

483

7.84

27.

864

8.45

98.

470

3.23

81.

073

4.05

71.

055

0.99

8

1.09

72.

024

0.97

81.

031

3.18

1

1.25

2

1.02

40.

977

0.98

1

1.00

2

1.00

0

 

N

HN

OH

OMeV

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 0 ppm

0.92

60.

942

1.24

81.

515

1.54

81.

562

1.57

81.

672

1.86

11.

940

1.96

21.

995

2.25

52.

275

2.29

52.

315

2.66

12.

704

2.72

62.

896

2.91

73.

333

3.95

95.

093

5.12

45.

136

5.14

95.

985

6.00

46.

011

6.02

96.

046

6.05

46.

072

7.26

37.

339

7.39

17.

397

7.41

47.

420

7.45

48.

037

8.06

08.

789

8.80

0

1.09

0

2.48

91.

134

1.09

81.

172

1.14

8

4.83

21.

975

0.94

3

3.31

5

2.01

1

1.07

0

3.12

0

1.07

3

1.00

0

 

N

HN

OMs

OMe

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 0 ppm

1.09

01.

104

1.12

41.

145

1.15

71.

352

1.37

51.

405

1.71

01.

729

1.74

71.

809

2.47

42.

489

3.18

53.

206

3.22

83.

274

3.30

13.

321

3.37

13.

394

3.41

53.

476

3.93

35.

168

5.19

35.

229

5.29

05.

348

5.37

25.

807

5.82

15.

833

5.84

95.

865

5.87

65.

891

7.26

07.

348

7.35

37.

371

7.37

67.

487

7.49

77.

572

7.99

88.

021

8.72

98.

739

1.25

71.

979

3.12

1

0.87

4

4.78

8

3.05

5

1.82

71.

121

0.86

2

1.09

60.

939

0.92

1

1.02

8

1.00

0

 

N

HN

OH

OMe

VI

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 0 ppm

1.26

71.

283

1.29

91.

623

1.64

41.

656

1.67

51.

693

1.71

01.

730

1.80

21.

819

1.83

41.

851

2.21

32.

225

2.77

82.

812

2.97

02.

992

3.02

23.

043

3.09

03.

111

3.14

33.

725

3.74

13.

758

5.93

2

7.26

47.

281

7.28

87.

304

7.31

07.

590

7.60

17.

656

7.66

17.

937

7.96

08.

683

8.69

4

9.39

1

3.00

01.

024

1.09

23.

197

1.26

81.

068

0.96

81.

195

0.98

5

1.88

5

0.97

4

1.25

21.

074

0.92

71.

404

1.16

3

1.27

4

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

7.19

4

22.5

2622

.901

27.3

0732

.662

45.7

9450

.081

53.5

3956

.379

72.3

1176

.685

77.0

0277

.320

104.

937

118.

693

122.

325

126.

508

131.

446

140.

723

143.

115

146.

703

156.

671

 

N

HN

O

OHVII

N

HN

O

OHVII

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 0 ppm

1.22

01.

236

1.25

01.

442

1.45

71.

489

1.50

51.

594

1.61

11.

631

1.70

31.

720

1.73

41.

751

2.09

12.

102

2.11

22.

564

2.59

82.

611

2.92

82.

948

3.43

73.

837

3.85

33.

940

5.87

2

7.12

87.

263

7.31

07.

333

7.67

67.

686

7.94

07.

950

7.96

47.

982

8.00

58.

728

8.73

9

3.00

01.

195

1.24

63.

022

1.19

21.

056

1.02

4

1.94

2

1.15

7

1.22

03.

139

0.97

6

1.16

31.

462

0.92

6

1.09

8

0.91

3

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

7.34

4

23.6

8924

.453

27.4

2032

.925

46.8

4754

.902

55.8

5056

.181

73.2

5676

.683

77.0

0177

.247

77.3

19

100.

690

119.

375

121.

416

126.

520

131.

820

143.

208

144.

096

147.

717

157.

837

 

N

HN

O

OMeVIII

N

HN

O

OMeVIII

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10 9 8 7 6 5 4 3 2 1 0 ppm

1.60

2

7.26

48.

078

8.08

38.

086

8.09

08.

094

8.09

88.

101

8.33

28.

340

8.34

8

2.05

22.

000

 

 

N

N

Cl

Cl

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 0 ppm

1.23

71.

255

1.27

31.

510

1.53

11.

543

1.80

72.

055

2.08

12.

112

2.20

02.

220

2.66

72.

678

2.68

92.

700

2.72

32.

803

2.83

62.

861

2.92

12.

941

3.39

43.

410

3.90

14.

954

4.98

75.

935

7.02

17.

035

7.34

37.

348

7.36

67.

371

7.40

97.

420

7.53

17.

535

7.91

97.

927

7.93

47.

941

7.97

57.

998

8.33

08.

338

8.34

48.

352

8.62

98.

640

1.82

46.

318

1.91

34.

432

2.02

9

2.43

64.

127

2.11

5

2.11

5

5.61

2

3.53

1

1.78

4

1.60

72.

292

1.81

72.

073

2.05

32.

140

1.94

5

2.00

0

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

23.2

3626

.492

27.7

62

39.6

70

49.4

7549

.836

55.6

3660

.080

76.1

4976

.682

77.0

0077

.317

101.

992

114.

630

118.

273

121.

848

122.

426

123.

010

127.

260

131.

542

132.

125

140.

336

144.

664

144.

875

147.

350

156.

384

157.

643

 

N

HN

O

OMe

R' =OR'

OR'

N

N

IX

N

HN

O

OMe

R' =OR'

OR'

N

N

IX

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 ppm

0.77

31.

151

1.15

71.

168

1.17

51.

186

1.19

31.

351

1.37

01.

681

1.71

82.

292

2.32

52.

542

2.56

82.

592

2.95

62.

982

2.98

93.

014

3.44

33.

476

3.51

03.

831

5.26

95.

505

7.20

27.

229

7.23

47.

260

7.44

07.

451

7.83

67.

858

8.42

18.

432

3.06

8

2.03

33.

240

3.04

3

1.02

41.

067

2.07

2

1.00

4

2.96

8

1.06

6

1.90

60.

990

1.00

4

1.00

0

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

11.9

80

21.0

3925

.352

27.5

7328

.104

37.3

61

43.2

68

55.6

3758

.485

59.6

89

71.5

1476

.683

77.0

0177

.318

101.

381

118.

458

121.

234

126.

517

131.

124

143.

844

147.

244

148.

382

157.

556

 

NH

OHN

OMe

NH

OHN

OMe

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 0 ppm

1.27

41.

347

1.37

51.

405

1.53

31.

561

1.58

71.

813

1.89

51.

912

1.94

22.

453

2.45

82.

486

2.75

12.

764

2.78

22.

793

2.85

42.

986

3.13

13.

157

3.19

03.

307

3.31

03.

777

3.79

93.

804

3.82

53.

831

4.93

85.

591

7.27

97.

283

7.31

87.

341

7.62

77.

638

7.88

67.

909

8.58

48.

595

3.00

0

2.07

11.

468

2.19

71.

022

2.01

4

0.96

0

1.02

8

1.88

9

0.93

5

0.89

2

0.87

30.

967

0.92

40.

930

0.97

7

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

12.1

8620

.869

26.5

5128

.169

28.3

3038

.128

44.4

8248

.363

48.5

7748

.789

49.0

0149

.214

49.4

2849

.641

59.0

1460

.890

71.5

20

105.

096

119.

853

123.

514

128.

299

131.

466

143.

876

147.

323

149.

157

158.

298

 

NH

OHN

OH

NH

OHN

OH

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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10 9 8 7 6 5 4 3 2 1 0 ppm

0.75

30.

771

0.78

91.

048

1.17

31.

192

1.21

01.

238

1.25

11.

630

1.66

31.

701

1.90

41.

915

1.96

11.

982

1.99

02.

012

2.09

12.

530

2.55

42.

571

2.58

92.

926

2.93

73.

181

3.20

33.

225

3.28

33.

311

3.34

23.

503

3.52

63.

608

3.63

04.

211

5.28

56.

075

6.88

17.

038

7.04

37.

061

7.06

67.

261

7.56

07.

571

7.66

97.

692

8.57

18.

582

3.00

09.

187

3.85

5

1.89

90.

987

0.94

60.

888

1.06

8

0.94

30.

995

0.97

91.

010

1.22

6

0.90

4

0.91

9

0.95

70.

969

0.97

60.

954

0.97

2

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

11.5

65

24.7

6426

.707

27.0

6831

.802

36.0

6943

.822

46.0

54

57.3

1958

.632

59.9

17

76.6

8477

.001

77.3

1978

.354

100.

394

118.

556

122.

152

125.

475

131.

079

143.

463

145.

033

146.

837

157.

743

 

NH

OHN

O

XII

NH

OHN

O

XII

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-16

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.65

7

4.50

04.

521

4.64

24.

651

4.67

74.

704

4.72

84.

877

4.88

26.

175

6.17

96.

191

6.19

47.

022

7.02

77.

037

7.04

27.

255

7.26

07.

272

7.33

47.

353

7.37

17.

394

7.41

37.

430

9.15

5

1.05

52.

116

1.05

8

1.00

0

1.07

9

4.85

2

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.1

33

43.8

32

65.1

1573

.277

76.6

8477

.002

77.3

1984

.338

127.

677

128.

600

128.

763

129.

378

134.

839

146.

163

149.

362

168.

275

 

NO2

NH

OBoc

3a

NO2

NH

OBoc

3a

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-17

 

 

 

NO2

NH

OBoc

rac-3a

NO2

NH

OBoc

3a

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 18: Organocatalytic asymmetric direct vinylogous Michael ... · Organocatalytic asymmetric direct vinylogous Michael addition of ... Department of Organic Chemistry, ... SI-Part-B, Page

Ray Choudhury & Mukherjee, SI-Part-B, Page S-18

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

NO2

NH

OBoc

ent-3a

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-19

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.64

3

2.33

4

4.45

64.

466

4.48

74.

497

4.58

14.

591

4.60

54.

615

4.62

44.

639

4.66

44.

669

4.69

34.

840

4.84

46.

149

6.15

26.

164

6.16

77.

024

7.02

87.

040

7.04

37.

122

7.14

27.

186

7.20

57.

263

9.04

1

3.11

1

1.05

12.

160

1.05

2

1.00

0

1.08

82.

209

2.10

7

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

20.9

61

28.0

34

43.4

67

65.1

4673

.361

76.6

8277

.000

77.3

1984

.128

127.

472

128.

544

129.

922

131.

633

138.

344

146.

331

149.

218

168.

273

 

NO2

NH

OBoc

Me

3b

NO2

NH

OBoc

Me

3b

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-20

 

 

 

NO2

NH

OBoc

Me

rac-3b

NO2

NH

OBoc

Me

3b

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-21

 

 

 

 

 

 

 

NO2

NH

OBoc

Me

ent-3b

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-22

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.64

5

4.52

14.

529

4.54

94.

556

4.59

84.

606

4.62

24.

630

4.64

04.

668

4.69

24.

856

4.86

06.

170

6.17

46.

186

6.18

97.

009

7.01

47.

025

7.02

97.

080

7.10

17.

123

7.22

37.

236

7.24

57.

260

9.02

9

0.96

42.

093

1.06

2

1.00

0

1.05

82.

134

1.98

8

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.0

68

43.3

02

64.8

7573

.573

76.6

7576

.993

77.3

1184

.376

116.

266

116.

482

128.

852

129.

355

129.

439

130.

456

130.

489

145.

971

149.

406

161.

257

163.

728

168.

042

 

NO2

NH

OBoc

F

3c

NO2

NH

OBoc

F

3c

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-23

 

 

 

NO2

NH

OBoc

F

rac-3c

NO2

NH

OBoc

F

3c

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 24: Organocatalytic asymmetric direct vinylogous Michael ... · Organocatalytic asymmetric direct vinylogous Michael addition of ... Department of Organic Chemistry, ... SI-Part-B, Page

Ray Choudhury & Mukherjee, SI-Part-B, Page S-24

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.63

1

4.51

24.

522

4.54

24.

552

4.58

34.

591

4.60

64.

615

4.62

34.

637

4.66

64.

689

4.84

46.

159

6.16

26.

174

6.17

76.

993

6.99

77.

008

7.01

27.

184

7.20

47.

260

7.36

37.

383

9.14

5

1.02

12.

253

1.08

4

1.00

0

1.10

32.

260

2.28

4

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.0

6029

.619

43.3

93

64.7

4373

.350

76.6

8277

.000

77.3

1884

.406

129.

022

129.

528

133.

218

134.

548

145.

879

149.

382

167.

983

 

NO2

NH

OBoc

Cl

3d

NO2

NH

OBoc

Cl

3d

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-25

 

 

 

NO2

NH

OBoc

Cl

rac-3d

NO2

NH

OBoc

Cl

3d

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-26

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.63

5

4.50

84.

519

4.53

84.

549

4.57

14.

580

4.59

44.

604

4.61

34.

635

4.65

84.

665

4.68

84.

845

6.16

36.

166

6.17

86.

181

6.99

16.

995

7.00

77.

010

7.12

77.

147

7.26

37.

521

7.54

2

9.01

5

0.94

42.

072

1.02

9

0.98

6

1.00

02.

213

2.04

5

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.0

74

43.4

64

64.6

6573

.277

76.6

9677

.014

77.3

3284

.431

122.

651

128.

923

129.

339

132.

497

133.

753

145.

871

149.

411

167.

966

 

NO2

NH

OBoc

Br

3e

NO2

NH

OBoc

Br

3e

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-27

 

 

 

NO2

NH

OBoc

Br

rac-3e

NO2

NH

OBoc

Br

3e

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-28

 

 

 

 

 

NO2

NH

OBoc

Br

ent-3e

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-29

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.65

5

3.81

2

6.16

86.

183

6.75

26.

796

6.82

36.

846

6.86

76.

914

6.93

56.

960

7.03

57.

039

7.05

17.

055

7.10

47.

126

7.16

57.

186

7.23

87.

264

7.27

6

8.28

5

3.05

1

1.00

01.

911

0.98

8

0.91

4

2.19

71.

057

2.63

0

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.1

44

43.3

13

55.3

23

65.2

3273

.707

76.6

8377

.000

77.3

1884

.266

114.

733

126.

521

128.

678

128.

843

146.

382

149.

442

159.

612

168.

232

 

NO2

NH

OBoc

OMe

3f

NO2

NH

OBoc

OMe

3f

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-30

 

 

 

NO2

NH

OBoc

OMe

rac-3f

NO2

NH

OBoc

OMe

3f

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-31

 

8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm

1.64

4

4.51

24.

522

4.54

24.

552

4.59

74.

607

4.62

14.

631

4.63

94.

651

4.68

14.

705

4.86

44.

868

6.18

66.

189

6.20

16.

204

7.01

67.

020

7.03

17.

035

7.13

97.

148

7.15

67.

174

7.32

47.

337

7.34

87.

351

9.23

5

1.00

92.

137

1.05

2

1.00

0

1.15

21.

640

2.35

6

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.0

78

43.5

25

64.7

0973

.137

76.6

8277

.000

77.3

1884

.467

125.

699

128.

034

128.

860

128.

981

130.

592

135.

263

136.

850

145.

790

149.

416

167.

902

 

NO2

NH

OBoc

Cl

3g

NO2

NH

OBoc

Cl

3g

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-32

 

 

 

 

NO2

NH

OBoc

Cl

rac-3g

NO2

NH

OBoc

Cl

3g

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-33

 

 

 

 

NO2

NH

OBoc

Cl

ent-3g

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-34

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.61

9

4.68

14.

694

4.70

24.

710

5.04

45.

048

5.05

95.

073

5.08

15.

095

6.10

36.

106

6.11

96.

947

6.95

16.

962

6.96

77.

055

7.07

67.

260

7.27

67.

282

7.29

87.

303

7.46

57.

470

9.12

5

1.98

8

2.03

4

1.00

0

1.02

81.

029

1.03

30.

966

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.1

02

40.4

24

62.0

29

73.7

5676

.676

76.9

9477

.312

84.5

80

127.

778

128.

608

128.

697

130.

529

130.

640

135.

149

135.

529

146.

348

149.

681

168.

166

 

NO2

NH

OBoc

Cl

Cl

3h

NO2

NH

OBoc

Cl

Cl

3h

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-35

 

 

 

 

NO2

NH

OBoc

Cl

Cl

rac-3h

NO2

NH

OBoc

Cl

Cl

3h

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-36

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.68

4

4.55

54.

580

4.60

04.

624

4.79

84.

822

4.84

24.

866

4.97

06.

177

6.18

16.

193

6.19

67.

050

7.05

47.

065

7.06

97.

260

7.37

47.

395

7.51

67.

527

7.53

67.

539

7.69

87.

815

7.82

87.

838

7.84

57.

860

7.88

67.

908

9.10

8

1.08

62.

118

1.09

1

1.00

0

1.10

31.

166

2.37

31.

171

2.25

81.

160

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.1

29

43.8

30

65.0

7173

.252

76.6

9577

.012

77.3

3084

.339

125.

280

126.

565

126.

733

126.

869

127.

711

127.

804

128.

761

129.

344

132.

255

132.

944

133.

217

146.

179

149.

401

168.

158

 

NO2

NH

OBoc

3i

NO2

NH

OBoc

3i

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-37

 

 

 

NO2

NH

OBoc

rac-3i

NO2

NH

OBoc

3i

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

Page 38: Organocatalytic asymmetric direct vinylogous Michael ... · Organocatalytic asymmetric direct vinylogous Michael addition of ... Department of Organic Chemistry, ... SI-Part-B, Page

Ray Choudhury & Mukherjee, SI-Part-B, Page S-38

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.60

8

4.30

84.

319

4.34

14.

352

4.50

84.

532

4.54

14.

566

4.72

34.

733

4.74

54.

757

4.76

84.

956

4.96

04.

965

6.19

66.

199

6.21

16.

214

6.29

66.

304

6.36

46.

368

6.37

67.

178

7.18

27.

193

7.19

77.

260

7.42

5

9.06

7

1.02

91.

100

1.05

11.

002

1.05

11.

060

1.02

9

1.00

00.

980

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

27.9

98

38.1

32

63.4

01

72.5

3476

.670

76.9

8877

.305

84.3

27

108.

853

110.

748

128.

634

143.

178

146.

843

148.

872

149.

076

168.

136

 

NO2

NH

OBoc

O

3j

NO2

NH

OBoc

O

3j

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-39

 

 

 

NO2

NH

OBoc

O

rac-3j

NO2

NH

OBoc

O

3j

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-40

 

 

 

 

NO2

NH

OBoc

O

ent-3j

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-41

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.64

7

4.48

74.

500

4.52

14.

533

4.55

74.

580

4.59

14.

614

4.89

64.

906

4.91

84.

929

4.94

14.

961

4.96

64.

970

6.20

26.

209

6.21

76.

225

6.98

56.

993

7.01

67.

018

7.03

07.

040

7.16

07.

164

7.17

67.

180

7.27

07.

313

7.32

5

9.07

3

1.00

01.

015

1.10

91.

031

0.97

3

0.99

31.

020

1.06

80.

975

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.0

95

39.8

70

64.8

8374

.973

76.6

8277

.000

77.3

1884

.454

125.

762

126.

344

127.

437

128.

974

137.

296

146.

312

149.

254

168.

110

 

NO2

NH

OBoc

S

3k

NO2

NH

OBoc

S

3k

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-42

 

 

 

NO2

NH

OBoc

S

rac-3k

NO2

NH

OBoc

S

3k

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-43

 

 

 

 

NO2

NH

OBoc

S

ent-3k

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-44

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.69

0

4.51

24.

525

4.54

54.

558

4.62

14.

645

4.65

44.

678

4.99

75.

008

5.01

95.

030

5.04

25.

134

5.13

95.

144

6.19

16.

194

6.20

66.

209

7.05

07.

055

7.06

67.

070

7.26

27.

317

7.33

57.

354

7.37

57.

396

7.41

47.

508

7.82

67.

846

8.13

28.

150

18.1

90

1.03

71.

028

1.08

41.

019

0.99

6

1.12

52.

273

1.02

61.

030

1.08

3

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

28.1

7228

.207

35.5

43

62.9

40

73.1

5776

.682

77.0

0077

.317

84.4

9984

.621

115.

396

115.

608

119.

199

122.

707

123.

225

125.

459

128.

921

135.

480

146.

610

149.

308

149.

734

167.

979

 

NO2

NH

OBoc

NBoc

3l

NO2

NH

OBoc

NBoc

3l

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-45

 

 

 

NO2

NH

OBoc

NBoc

rac-3l

NO2

NH

OBoc

NBoc

3l

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-46

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.57

31.

678

1.70

51.

770

1.80

01.

832

1.93

21.

961

3.16

23.

171

3.18

13.

190

3.20

03.

210

3.22

03.

859

3.86

93.

894

3.90

44.

109

4.12

74.

144

4.16

24.

952

4.95

64.

960

6.19

56.

210

7.08

67.

101

3.83

00.

999

1.33

69.

084

1.20

93.

077

1.04

5

0.98

4

1.00

21.

028

1.00

7

0.97

6

1.00

0

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

25.9

9528

.014

30.7

2430

.769

39.1

2942

.795

61.6

57

73.3

4376

.682

77.0

0077

.318

83.9

44

129.

179

146.

315

148.

927

168.

341

 

NO2

NH

OBoc3m

NO2

NH

OBoc3m

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-47

 

 

 

 

NO2

NH

OBocrac-3m

NO2

NH

OBoc3m

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-48

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.34

61.

359

1.37

71.

394

1.41

21.

543

1.65

21.

668

1.68

51.

701

1.71

91.

736

1.75

23.

330

3.34

93.

360

3.36

73.

372

3.37

83.

390

3.40

83.

933

3.95

13.

965

3.98

44.

063

4.07

64.

095

4.10

84.

737

4.74

24.

747

6.18

46.

187

6.20

06.

203

7.11

17.

115

7.12

77.

131

7.26

0

6.01

8

2.22

38.

598

1.08

8

1.00

0

1.02

81.

185

1.06

3

1.03

6

1.02

3

 

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

22.1

5522

.655

25.3

2127

.975

35.8

7939

.152

63.0

86

75.3

9976

.727

77.0

4677

.364

83.8

99

129.

071

145.

915

148.

990

168.

381

 

NO2

NH

OBoc

3n

NO2

NH

OBoc

3n

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-49

 

 

 

NO2

NH

OBoc

rac-3n

NO2

NH

OBoc

3n

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-50

 

 

 

 

NO2

NH

OBoc

ent-3n

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-51

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.05

31.

070

1.13

51.

152

1.56

91.

750

1.76

71.

785

1.80

51.

822

1.83

93.

101

3.11

13.

121

3.12

93.

139

3.15

03.

160

3.88

93.

899

3.92

33.

934

4.10

44.

121

4.13

84.

155

4.92

84.

932

6.20

06.

204

6.21

66.

219

7.08

97.

093

7.10

47.

109

7.26

1

3.00

02.

986

9.07

61.

029

0.98

8

0.99

01.

008

0.98

2

0.95

9

0.98

0

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

20.5

6320

.645

27.9

7229

.490

43.8

78

61.9

91

73.5

3376

.682

77.0

0077

.318

83.9

18

129.

239

146.

110

148.

887

168.

308

 

NO2

NH

OBoc

3o

NO2

NH

OBoc

3o

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-52

 

 

 

 

NO2

NH

OBoc

rac-3o

NO2

NH

OBoc

3o

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-53

 

10 9 8 7 6 5 4 3 2 1 0 ppm

1.60

42.

851

2.86

52.

898

2.91

33.

101

3.12

43.

149

3.17

24.

365

4.37

94.

392

4.40

44.

417

4.44

74.

476

4.50

24.

547

4.55

94.

577

4.58

84.

646

4.66

84.

683

4.69

74.

712

4.72

04.

735

4.74

14.

757

7.00

57.

025

7.04

57.

064

7.08

27.

172

7.19

07.

285

7.30

47.

324

9.10

4

1.06

91.

000

1.01

01.

039

1.02

52.

142

1.10

01.

029

1.21

31.

015

200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm

27.9

17

38.4

3339

.153

59.9

36

70.4

3675

.296

76.6

8277

.000

77.3

1884

.903

118.

218

124.

156

125.

162

129.

403

130.

214

149.

162

154.

644

170.

225

 

NO2

NH

OBoc

OH H

4

NO2

NH

OBoc

OH H

4

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

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Ray Choudhury & Mukherjee, SI-Part-B, Page S-54

 

 

 

NO2

NH

OBoc

OH H

rac-4

NO2

NH

OBoc

OH H

4

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012