Journal of Organic Chemistry, volume 76, issue 7, pages 2350-2354
Enhanced anti-Diastereo- and Enantioselectivity in Alcohol-Mediated Carbonyl Crotylation Using an Isolable Single Component Iridium Catalyst
Publication type: Journal Article
Publication date: 2011-03-04
Journal:
Journal of Organic Chemistry
Q2
Q1
SJR: 0.724
CiteScore: 6.2
Impact factor: 3.3
ISSN: 00223263, 15206904
PubMed ID:
21375283
Organic Chemistry
Abstract
The cyclometalated iridium complex (S)-I derived from [Ir(cod)Cl](2), 4-cyano-3-nitrobenzoic acid, allyl acetate, and (S)-SEGPHOS is conveniently isolated by precipitation or through conventional silica gel flash chromatography. This single-component precatalyst allows alcohol mediated carbonyl crotylations to be performed at significantly lower temperature, resulting in enhanced levels of anti-diastereo- and enantioselectivity. Most significantly, the chromatographically isolated precatalyst (S)-I enables carbonyl crotylations that are not possible under previously reported conditions involving in situ generation of (S)-I.
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Gao X., Townsend I. A., Krische M. J. Enhanced anti-Diastereo- and Enantioselectivity in Alcohol-Mediated Carbonyl Crotylation Using an Isolable Single Component Iridium Catalyst // Journal of Organic Chemistry. 2011. Vol. 76. No. 7. pp. 2350-2354.
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Gao X., Townsend I. A., Krische M. J. Enhanced anti-Diastereo- and Enantioselectivity in Alcohol-Mediated Carbonyl Crotylation Using an Isolable Single Component Iridium Catalyst // Journal of Organic Chemistry. 2011. Vol. 76. No. 7. pp. 2350-2354.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo200068q
UR - https://doi.org/10.1021/jo200068q
TI - Enhanced anti-Diastereo- and Enantioselectivity in Alcohol-Mediated Carbonyl Crotylation Using an Isolable Single Component Iridium Catalyst
T2 - Journal of Organic Chemistry
AU - Gao, Xin
AU - Townsend, Ian A
AU - Krische, Michael J
PY - 2011
DA - 2011/03/04
PB - American Chemical Society (ACS)
SP - 2350-2354
IS - 7
VL - 76
PMID - 21375283
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2011_Gao,
author = {Xin Gao and Ian A Townsend and Michael J Krische},
title = {Enhanced anti-Diastereo- and Enantioselectivity in Alcohol-Mediated Carbonyl Crotylation Using an Isolable Single Component Iridium Catalyst},
journal = {Journal of Organic Chemistry},
year = {2011},
volume = {76},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jo200068q},
number = {7},
pages = {2350--2354},
doi = {10.1021/jo200068q}
}
Cite this
MLA
Copy
Gao, Xin, et al. “Enhanced anti-Diastereo- and Enantioselectivity in Alcohol-Mediated Carbonyl Crotylation Using an Isolable Single Component Iridium Catalyst.” Journal of Organic Chemistry, vol. 76, no. 7, Mar. 2011, pp. 2350-2354. https://doi.org/10.1021/jo200068q.