APPENDIX 1 - thesis.library.caltech.eduthesis.library.caltech.edu/8869/5/appendix 1 2.pdf ·...
77
Appendix 1 – Spectra Relevant to Chapter 1 APPENDIX 1 Spectra Relevant to Chapter 1: Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation 60
Transcript of APPENDIX 1 - thesis.library.caltech.eduthesis.library.caltech.edu/8869/5/appendix 1 2.pdf ·...
Appendix 1 – Spectra Relevant to Chapter 1
APPENDIX 1
Spectra Relevant to Chapter 1:
Enantioselective Construction of α-Quaternary Cyclobutanones by
Catalytic Asymmetric Allylic Alkylation
60
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.1
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 48
.
OO
O
48Ph
61
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.2 Infrared spectrum (thin film/NaCl) of compound 48
Figure A1.3 13C NMR (75 MHz, CDCl3) of compound 48
62
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.4
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 39a.
OEt
O
O
Ph
39a
63
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.5 Infrared spectrum (thin film/NaCl) of compound 39a
Figure A1.6 13C NMR (125 MHz, CDCl3) of compound 39a
64
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.7
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 39b.
OMe
O
O
Ph
39b
65
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.8 Infrared spectrum (thin film/NaCl) of compound 39b.
Figure A1.9 13C NMR (125 MHz, CDCl3) of compound 39b.
66
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.10
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 39c.
OBn
O
O
Ph
39c
67
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.11 Infrared spectrum (thin film/NaCl) of compound 39c.
Figure A1.12 13C NMR (125 MHz, CDCl3) of compound 39c.
68
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.13
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 39d.
OO
O
Ph
F 39d
69
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.14 Infrared spectrum (thin film/NaCl) of compound 39d.
Figure A1.15 13C NMR (125 MHz, CDCl3) of compound 39d.
70
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.16
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 39e.
OO
O
Ph
OMe
39e
71
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.17 Infrared spectrum (thin film/NaCl) of compound 39e.
Figure A1.18 13C NMR (125 MHz, CDCl3) of compound 39e.
72
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.19
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 39f.
OO
O
Ph
39f
73
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200ppm
Figure A1.20 Infrared spectrum (thin film/NaCl) of compound 39f.
Figure A1.21 13C NMR (125 MHz, CDCl3) of compound 39f.
74
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.22
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 39g.
OO
O
Ph
TMS
39g
75
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200ppm
Figure A1.23 Infrared spectrum (thin film/NaCl) of compound 39g.
Figure A1.24 13C NMR (125 MHz, CDCl3) of compound 39g.
76
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.25
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 39h.
OO
O
Ph
O
39h
77
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.26 Infrared spectrum (thin film/NaCl) of compound 39h.
Figure A1.27 13C NMR (125 MHz, CDCl3) of compound 39h.
78
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.28
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 41a.
BnO
OO
41a
79
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.29 Infrared spectrum (thin film/NaCl) of compound 41a.
Figure A1.30 13C NMR (125 MHz, CDCl3) of compound 41a.
80
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.31
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 41b.
BnO
OMe
O
41b
81
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.32 Infrared spectrum (thin film/NaCl) of compound 41b.
Figure A1.33 13C NMR (125 MHz, CDCl3) of compound 41b.
82
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.34
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 41c.
BnO
OCl
O
41c
83
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.35 Infrared spectrum (thin film/NaCl) of compound 41c.
Figure A1.36 13C NMR (125 MHz, CDCl3) of compound 41c.
84
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.37
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 36
.
BnO
OO
36
85
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.38 Infrared spectrum (thin film/NaCl) of compound 36.
Figure A1.39 13C NMR (125 MHz, CDCl3) of compound 36.
86
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.40
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 41d.
BnO
OO
OBn
41d
87
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200ppm
Figure A1.41 Infrared spectrum (thin film/NaCl) of compound 41d.
Figure A1.42 13C NMR (125 MHz, CDCl3) of compound 41d.
88
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.43
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 41e.
BnO
OO
OMe
41e
89
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200ppm
Figure A1.44 Infrared spectrum (thin film/NaCl) of compound 41e.
Figure A1.45 13C NMR (125 MHz, CDCl3) of compound 41e.
90
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.46
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 41f.
BnO
OO
F41f
91
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.47 Infrared spectrum (thin film/NaCl) of compound 41f.
Figure A1.48 13C NMR (125 MHz, CDCl3) of compound 41f.
92
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.49
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 40a.
OEt
Ph40a
93
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.50 Infrared spectrum (thin film/NaCl) of compound 40a.
Figure A1.51 13C NMR (125 MHz, CDCl3) of compound 40a.
94
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.52
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 40b.
OMe
Ph40b
95
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.53 Infrared spectrum (thin film/NaCl) of compound 40b.
Figure A1.54 13C NMR (125 MHz, CDCl3) of compound 40b.
96
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.55
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 40c.
O
Ph
Ph
40c
97
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.56 Infrared spectrum (thin film/NaCl) of compound 40c.
Figure A1.57 13C NMR (125 MHz, CDCl3) of compound 40c.
98
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.58
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 40d.
O
Ph
F
40d
99
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.59 Infrared spectrum (thin film/NaCl) of compound 40d.
Figure A1.60 13C NMR (125 MHz, CDCl3) of compound 40d.
100
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.61
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 40e.
OBn
O
O
Ph
39c
101
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.62 Infrared spectrum (thin film/NaCl) of compound 40e.
Figure A1.63 13C NMR (125 MHz, CDCl3) of compound 40e.
102
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.64
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 40f.
O
Ph40f
103
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.65 Infrared spectrum (thin film/NaCl) of compound 40f.
Figure A1.66 13C NMR (125 MHz, CDCl3) of compound 40f.
104
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.67
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 40g.
O
Ph
40g
TMS
105
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.68 Infrared spectrum (thin film/NaCl) of compound 40g.
Figure A1.69 13C NMR (125 MHz, CDCl3) of compound 40g.
106
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.70
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 40h.
O
Ph
O 40h
107
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.71 Infrared spectrum (thin film/NaCl) of compound 40h.
Figure A1.72 13C NMR (125 MHz, CDCl3) of compound 40h.
108
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.73
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 42a.
OBn 42a
109
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.74 Infrared spectrum (thin film/NaCl) of compound 42a.
Figure A1.75 13C NMR (125 MHz, CDCl3) of compound 42a.
110
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.76
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 42b.
OBn
Me
42b
111
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.77 Infrared spectrum (thin film/NaCl) of compound 42b.
Figure A1.78 13C NMR (125 MHz, CDCl3) of compound 42b.
112
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.79
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 42c.
OBn
Cl
42c
113
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.80 Infrared spectrum (thin film/NaCl) of compound 42c.
Figure A1.81 13C NMR (125 MHz, CDCl3) of compound 42c.
114
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.82
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 38
.
OBn 38
115
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.83 Infrared spectrum (thin film/NaCl) of compound 38.
Figure A1.84 13C NMR (125 MHz, CDCl3) of compound 38.
116
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.85
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 42d.
OBn
42d
OBn
117
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.86 Infrared spectrum (thin film/NaCl) of compound 42d.
Figure A1.87 13C NMR (125 MHz, CDCl3) of compound 42d.
118
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.88
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 49
.
OO
49
Bn
OBn
119
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200ppm
Figure A1.89 Infrared spectrum (thin film/NaCl) of compound 49.
Figure A1.90 13C NMR (125 MHz, CDCl3) of compound 49.
120
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.91
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 42e.
OBn
42e
OMe
121
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.92 Infrared spectrum (thin film/NaCl) of compound 42e.
Figure A1.93 13C NMR (125 MHz, CDCl3) of compound 42e.
122
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.94
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 42f.
OBn 42f
F
123
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.95 Infrared spectrum (thin film/NaCl) of compound 42f.
Figure A1.96 13C NMR (125 MHz, CDCl3) of compound 42f.
124
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.97
1 H N
MR
(500
MH
z, C
DC
l 3) o
f com
poun
d 44
.
OO
Ph
Ph
44
125
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.98 Infrared spectrum (thin film/NaCl) of compound 44.
Figure A1.99 13C NMR (125 MHz, CDCl3) of compound 44.
126
Appendix 1 – Spectra Relevant to Chapter 1
Figu
re A
1.10
0 1 H
NM
R (5
00 M
Hz,
CD
Cl 3)
of c
ompo
und 45
.
PhTMS
O
45
01
23
45
67
89
10
ppm
127
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.101 Infrared spectrum (thin film/NaCl) of compound 45.
Figure A1.102 13C NMR (125 MHz, CDCl3) of compound 45.
128
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.10
3 1 H
NM
R (5
00 M
Hz,
CD
Cl 3)
of c
ompo
und 46
.
H NPh
OF
46
129
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.104 Infrared spectrum (thin film/NaCl) of compound 46.
Figure A1.105 13C NMR (125 MHz, CDCl3) of compound 46.
130
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.10
6 1 H
NM
R (5
00 M
Hz,
CD
Cl 3)
of c
ompo
und 47
.
OPh
47
131
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.107 Infrared spectrum (thin film/NaCl) of compound 47.
Figure A1.108 13C NMR (125 MHz, CDCl3) of compound 47.
132
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.10
9 1 H
NM
R (5
00 M
Hz,
CD
Cl 3)
of c
ompo
und 51
.
OMeO
O
51
133
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.110 Infrared spectrum (thin film/NaCl) of compound 51.
Figure A1.111 13C NMR (125 MHz, CDCl3) of compound 51.
134
Appendix 1 – Spectra Relevant to Chapter 1
01
23
45
67
89
10
ppm
Figu
re A
1.11
2 1 H
NM
R (5
00 M
Hz,
CD
Cl 3)
of c
ompo
und 52
.
OMe 52
135
Appendix 1 – Spectra Relevant to Chapter 1
020406080100120140160180200220ppm
Figure A1.113 Infrared spectrum (thin film/NaCl) of compound 52.
Figure A1.114 13C NMR (125 MHz, CDCl3) of compound 52.
136
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