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Enantioselective Organocatalytic Amine Conjugate Addition

Chen, Young K. and Yoshida, Masanori and MacMillan, David W. C. (2006) Enantioselective Organocatalytic Amine Conjugate Addition. Journal of the American Chemical Society, 128 (29). pp. 9328-9329. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170420-160603226

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Abstract

The first enantioselective organocatalytic amine conjugate addition has been successfully developed. The application of LUMO-lowering iminium catalysis has enabled the highly chemo- and enantioselective 1,4-addition of a rationally designed N-silyloxycarbamate nucleophile (HOMO-raised) to α,β-unsaturated aldehydes. Imidazolidinone 2•pTSA was found to catalyze the addition of various orthogonally N-protected silyloxycarbamate nucleophiles to a range of α,β-unsaturated aldehydes, affording synthetically useful β-amino aldehyde intermediates. The synthetic utility of the protocol was demonstrated in the rapid synthesis of enantioenriched β-amino acids in one operation and 1,3-amino alcohol derivatives in three operations.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja063267sDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja063267sPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja063267sPublisherSupporting Information
Additional Information:© 2006 American Chemical Society. Received May 10, 2006. Publication Date (Web): June 30, 2006. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from Amgen and Merck. Y.K.C. thanks the National Cancer Institute for a postdoctoral fellowship (1 F32 CA108376-01).
Funders:
Funding AgencyGrant Number
NIHR01 GM66142-01
AmgenUNSPECIFIED
MerckUNSPECIFIED
NIH postdoctoral fellowship1 F32 CA108376-01
National Cancer InstituteUNSPECIFIED
Issue or Number:29
Record Number:CaltechAUTHORS:20170420-160603226
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170420-160603226
Official Citation:Enantioselective Organocatalytic Amine Conjugate Addition Young K. Chen, Masanori Yoshida, and David W. C. MacMillan Journal of the American Chemical Society 2006 128 (29), 9328-9329 DOI: 10.1021/ja063267s
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76788
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:21 Apr 2017 00:15
Last Modified:03 Oct 2019 17:50

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