Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated...

Supporting Information

Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylates

John Kallikat Augustine,* a Agnes Bombrun,b Srinivasa Venkatachaliah,a Anandh Jothia

aSyngene International Ltd., Biocon Park, Plot Nos. 2 & 3, Bommasandra IV Phase, Jigani Link

Road, Bangalore - 560 099, India.

bCovance Central Laboratory Services, 7 Rue Moise-Marcinhes, 1217 Meyrin, Geneva, Switzerland.

john.kallikat@syngeneintl.com

Table of contents

Table of contents.………………………………………………….... 1 1H NMR, 13C NMR, HPLC and IR reports for 1aE…….………… 2-5 1H NMR, 13C NMR, HPLC and IR reports for 1a-1q…….………… 6-73 1H NMR, 13C NMR, HPLC and IR reports for 2a-2j……….………. 74-113 1H NMR, 13C NMR, HPLC and IR reports for 3a-3i……….………. 114-149 1H NMR, 13C NMR, HPLC and IR reports for 4a-4j……….………. 150-189 1H NMR, 13C NMR reports for 5 …………………….……….……. 190-191

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2013

(E)-isomer (1aE): 1H NMR (400 MHz) in DMSO-d6

BrCOOMe

delta 7.54 ppm

13C NMR (100 MHz) in CDCl3 (1aE)

BrCOOMe

IR data (1aE)

BrCOOMe

HPLC data (1aE)

BrCOOMe

(Z)-isomer (1a): 1H NMR (400 MHz) in DMSO-d6

delta 8.25 ppm

13C NMR (100 MHz) in CDCl3 (1a)

IR spectrum (1a)

HPLC data (1a)

1H NMR (400 MHz) in CDCl3 (1b)

13C NMR (100 MHz) in CDCl3 (1b)

IR spectrum (1b)

HPLC data (1b)

1H NMR (400 MHz) in CDCl3 (1c)

13C NMR (100 MHz) in CDCl3 (1c)

IR spectrum (1c)

HPLC data (1c)

1H NMR (400 MHz) in DMSO-d6 (1d)

13C NMR (100 MHz) in CDCl3 (1d)

IR spectrum (1d)

HPLC data (1d)

1H NMR (400 MHz) in CDCl3 (1e)

13C NMR (100 MHz) in CDCl3 (1e)

IR spectrum (1e)

HPLC data (1e)

1H NMR (400 MHz) in CDCl3 (1f)

13C NMR (100 MHz) in CDCl3 (1f)

IR spectrum (1f)

HPLC data (1f)

1H NMR (400 MHz) in CDCl3 (1g)

13C NMR (100 MHz) in CDCl3 (1g)

IR spectrum (1g)

HPLC data (1g)

1H NMR (400 MHz) in CDCl3 (1h)

13C NMR (100 MHz) in CDCl3 (1h)

IR spectrum (1h)

HPLC data (1h)

1H NMR (400 MHz) in DMSO-d6 (1i)

13C NMR (100 MHz) in DMSO-d6 (1i)

IR spectrum (1i)

HPLC data (1i)

1H NMR (400 MHz) in CDCl3 (1j)

13C NMR (100 MHz) in CDCl3 (1j)

IR spectrum (1j)

HPLC data (1j)

1H NMR (400 MHz) in CDCl3 (1k)

(1k)Br

COOMeSBr

13C NMR (100 MHz) in CDCl3 (1k)

(1k)Br

COOMeSBr

IR spectrum (1k)

(1k)Br

COOMeSBr

HPLC data (1k)

(1k)Br

COOMeSBr

1H NMR (400 MHz) in CDCl3 (1l)

(1l)Br

COOMeO

13C NMR (100 MHz) in CDCl3 (1l)

(1l)Br

COOMeO

IR spectrum (1l)

(1l)Br

COOMeO

HPLC data (1l)

(1l)Br

COOMeO

1H NMR (400 MHz) in CDCl3 (1m)

13C NMR (100 MHz) in CDCl3 (1m)

IR spectrum (1m)

HPLC data (1m)

1H NMR (400 MHz) in CDCl3 (1n)

13C NMR (100 MHz) in CDCl3 (1n)

IR spectrum (1n)

HPLC data (1n)

1H NMR (400 MHz) in CDCl3 (1o)

13C NMR (100 MHz) in CDCl3 (1o)

IR spectrum (1o)

HPLC data (1o)

1H NMR (400 MHz) in CDCl3 (1p)

13C NMR (100 MHz) in CDCl3 (1p)

IR spectrum (1p)

HPLC data (1p)

1H NMR (400 MHz) in DMSO-d6 (1q)

13C NMR (100 MHz) in DMSO-d6 (1q)

IR spectrum (1q)

HPLC data (1q)

1H NMR (400 MHz) in DMSO-d6 (2a)

13C NMR (100 MHz) in DMSO-d6 (2a)

IR spectrum (2a)

HPLC data (2a)

1H NMR (400 MHz) in DMSO-d6 (2b)

Br(2b)

13C NMR (100 MHz) in DMSO-d6 (2b)

Br(2b)

IR spectrum (2b)

Br(2b)

HPLC data (2b)

Br(2b)

1H NMR (400 MHz) in DMSO-d6 (2c)

13C NMR (100 MHz) in DMSO-d6 (2c)

IR spectrum (2c)

HPLC data (2c)

1H NMR (400 MHz) in CDCl3 (2d)

IR spectrum (2d)

HPLC data (2d)

(Z)NO2

IR spectrum (2e)

(Z)NO2

HPLC data (2e)

(Z)NO2

1H NMR (400 MHz) in DMSO-d6 (2f)

13C NMR (100 MHz) in DMSO-d6 (2f)

IR spectrum (2f)

HPLC data (2f)

1H NMR (400 MHz) in DMSO-d6 (2g)

13C NMR (100 MHz) in DMSO-d6 (2g)

IR spectrum (2g)

HPLC data (2g)

IR spectrum (2h)

HPLC data (2h)

1H NMR (400 MHz) in CDCl3 (2i)

13C NMR (100 MHz) in CDCl3 (2i)

IR spectrum (2i)

HPLC data (2i)

IR spectrum (2j)

HPLC data (2j)

1H NMR (400 MHz) in CDCl3 (3a)

13C NMR (100 MHz) in CDCl3 (3a)

IR spectrum (3a)

HPLC data (3a)

13C NMR (100 MHz) in CDCl3 (3b)

IR spectrum (3b)

HPLC data (3b)

IR spectrum (3c)

HPLC data (3c)

IR spectrum (3d)

HPLC data (3d)

IR spectrum (3e)

HPLC data (3e)

IR spectrum (3f)

HPLC spectrum (3f)

IR spectrum (3g)

HPLC data (3g)

IR spectrum (3h)

HPLC data (3h)

IR spectrum (3i)

HPLC data (3i)

1H NMR (400 MHz) in CDCl3 (4a)

13c NMR (100 MHz) in CDCl3 (4a)

IR spectrum (4a)

HPLC spectrum (4a)

13c NMR (100 MHz) in CDCl3 (4b)

IR spectrum (4b)

HPLC data (4b)

IR spectrum (4c)

HPLC data (4c)

IR spectrum (4d)

HPLC data (4d)

IR spectrum (4e)

HPLC data (4e)

IR spectrum (4f)

HPLC data (4f)

IR spectrum (4g)

HPLC data (4g)

1H NMR (400 MHz) in DMSO-d6 (4h)

13C NMR (100 MHz) in DMSO-d6 (4h)

IR spectrum (4h)

HPLC data (4h)

IR spectrum (4i)

HPLC data (4i)

IR spectrum (4j)

HPLC data (4j)

1H NMR (400 MHz) in CDCl3 (5)

13C NMR (100 MHz) in CDCl3 (5)

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Supporting Information - Semantic Scholar€¦ · 1 Supporting Information Titanium mediated...

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