Journal of the American Chemical Society, volume 131, issue 7, pages 2514-2520
anti-Diastereo- and Enantioselective Carbonyl Crotylation from the Alcohol or Aldehyde Oxidation Level Employing a Cyclometallated Iridium Catalyst: α-Methyl Allyl Acetate as a Surrogate to Preformed Crotylmetal Reagents
Publication type: Journal Article
Publication date: 2009-02-03
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Under the conditions of transfer hydrogenation employing an ortho-cyclometallated iridium catalyst generated in situ from [Ir(cod)Cl](2), 4-cyano-3-nitrobenzoic acid and the chiral phosphine ligand (S)-SEGPHOS, alpha-methyl allyl acetate couples to alcohols 1a-1j with complete levels of branched regioselectivity to furnish products of carbonyl crotylation 3a-3j, which are formed with good levels of anti-diastereoselectivity and exceptional levels of enantioselectivity. An identical set of optically enriched carbonyl crotylation products 3a-3j is accessible from the corresponding aldehydes 2a-2j under the same conditions, but employing isopropanol as the terminal reductant. Experiments aimed at probing the origins of stereoselection establish a matched mode of ionization for the (R)-acetate and the iridium catalyst modified by (S)-SEGPHOS, as well as reversible ionization of the allylic acetate with rapid pi-facial interconversion of the resulting pi-crotyl intermediate in advance of C-C bond formation. Additionally, rapid alcohol-aldehyde redox equilibration in advance of carbonyl addition is demonstrated. Thus, anti-diastereo- and enantioselective carbonyl crotylation from the alcohol or aldehyde oxidation level is achieved in the absence of any stoichiometric metallic reagents or stoichiometric metallic byproducts.
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Citations by publishers
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American Chemical Society (ACS)
75 publications, 44.12%
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1 publication, 0.59%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 0.59%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Kim I. S., Han S. B., Krische M. J. anti-Diastereo- and Enantioselective Carbonyl Crotylation from the Alcohol or Aldehyde Oxidation Level Employing a Cyclometallated Iridium Catalyst: α-Methyl Allyl Acetate as a Surrogate to Preformed Crotylmetal Reagents // Journal of the American Chemical Society. 2009. Vol. 131. No. 7. pp. 2514-2520.
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Kim I. S., Han S. B., Krische M. J. anti-Diastereo- and Enantioselective Carbonyl Crotylation from the Alcohol or Aldehyde Oxidation Level Employing a Cyclometallated Iridium Catalyst: α-Methyl Allyl Acetate as a Surrogate to Preformed Crotylmetal Reagents // Journal of the American Chemical Society. 2009. Vol. 131. No. 7. pp. 2514-2520.
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TY - JOUR
DO - 10.1021/ja808857w
UR - https://doi.org/10.1021/ja808857w
TI - anti-Diastereo- and Enantioselective Carbonyl Crotylation from the Alcohol or Aldehyde Oxidation Level Employing a Cyclometallated Iridium Catalyst: α-Methyl Allyl Acetate as a Surrogate to Preformed Crotylmetal Reagents
T2 - Journal of the American Chemical Society
AU - Han, Soo Bong
AU - Kim, In Su
AU - Krische, Michael J
PY - 2009
DA - 2009/02/03 00:00:00
PB - American Chemical Society (ACS)
SP - 2514-2520
IS - 7
VL - 131
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2009_Kim,
author = {Soo Bong Han and In Su Kim and Michael J Krische},
title = {anti-Diastereo- and Enantioselective Carbonyl Crotylation from the Alcohol or Aldehyde Oxidation Level Employing a Cyclometallated Iridium Catalyst: α-Methyl Allyl Acetate as a Surrogate to Preformed Crotylmetal Reagents},
journal = {Journal of the American Chemical Society},
year = {2009},
volume = {131},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/ja808857w},
number = {7},
pages = {2514--2520},
doi = {10.1021/ja808857w}
}
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Kim, In Su, et al. “anti-Diastereo- and Enantioselective Carbonyl Crotylation from the Alcohol or Aldehyde Oxidation Level Employing a Cyclometallated Iridium Catalyst: α-Methyl Allyl Acetate as a Surrogate to Preformed Crotylmetal Reagents.” Journal of the American Chemical Society, vol. 131, no. 7, Feb. 2009, pp. 2514-2520. https://doi.org/10.1021/ja808857w.