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Development of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with α,β-unsaturated aldehydes

Borths, Christopher J. and Carrera, Diane E. and MacMillan, David W. C. (2009) Development of a general, enantioselective organocatalytic Mukaiyama-Michael reaction with α,β-unsaturated aldehydes. Tetrahedron, 65 (33). pp. 6746-6753. ISSN 0040-4020. PMCID PMC4158731. https://resolver.caltech.edu/CaltechAUTHORS:20090817-140019759

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Abstract

LUMO-lowering organocatalysis has been extended to promote the conjugate addition of S-alkyl and 1-pyrrolyl silylketene acetals to α,β-unsaturated aldehydes, yielding both, syn and anti Mukaiyama–Michael products with high levels of enantioselectivity. This strategy allows for the generation of chemically useful 1,5-dicarbonyl systems and again highlights the utility of organocatalysis.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/j.tet.2009.06.066DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040402009009260?via%3DihubPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4158731PubMed CentralArticle
Additional Information:Copyright © 2009 Published by Elsevier Ltd. Received 16 June 2009; revised 17 June 2009; accepted 18 June 2009. Available online 23 June 2009. This paper is dedicated to Professor Larry E. Overman on the occasion of being the 2009 recipient of the Tetrahedron Prize. A great scientist, scholar, teacher and friend and a class act in every way. This manuscript is also dedicated to Miss D.D. Turner of the E.H.S. for her continued efforts towards safe practices in the laboratory. Financial support was provided by the NIHGMS (R01 GM078201-01-01) and kind gifts from Amgen and Merck.
Funders:
Funding AgencyGrant Number
National Institute of General Medical SciencesR01 GM078201-01-01
AmgenUNSPECIFIED
MerckUNSPECIFIED
Subject Keywords:Mukaiyama–Michael; Enantioselective organocatalysis
Issue or Number:33
PubMed Central ID:PMC4158731
Record Number:CaltechAUTHORS:20090817-140019759
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20090817-140019759
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:15072
Collection:CaltechAUTHORS
Deposited By: Katherine Johnson
Deposited On:18 Aug 2009 16:20
Last Modified:03 Oct 2019 00:54

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