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The First Enantioselective Organocatalytic Mukaiyama−Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture

Brown, Sean P. and Goodwin, Nicole C. and MacMillan, David W. C. (2003) The First Enantioselective Organocatalytic Mukaiyama−Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture. Journal of the American Chemical Society, 125 (5). pp. 1192-1194. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20170417-065654426

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Abstract

The first enantioselective organocatalytic Mukaiyama−Michael reaction using α,β-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective addition of 2-silyloxy furans to unsaturated aldehydes to generate a variety of butenolide systems, an important chiral synthon found among many natural isolates. The (2S,5S)-5-benzyl-2-tert-butyl-imidazolidinone amine catalyst has been found to mediate the conjugate addition of a wide variety of substituted and unsubstituted silyloxy furans to unsaturated aldehydes. A diverse range of aldehyde substrates can be accommodated in this new organocatalytic transformation. Application of this new asymmetric technology to the enantioselective total synthesis of spiculisporic acid and the corresponding 5-epi-spiculisporic acid analogue is also discussed.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja029095qDOIArticle
http://pubs.acs.org/doi/full/10.1021/ja029095qPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja029095qPublisherSupporting Information
Additional Information:© 2003 American Chemical Society. Received 25 October 2002. Published online 10 January 2003. Published in print 1 February 2003. Financial support was provided by the NIHGMS (R01 GM66142-01) and kind gifts from AstraZeneca, Boehringer-Ingelheim, Bristol-Myers Squibb, Dupont, GlaxoSmithKline, Johnson and Johnson, Lilly, Materia, Merck Research Laboratories, Pfizer, Pharmacia, and Roche Biosciences. We also thank Great Lakes for their generous donation of (S)-phenylalanine. D.W.C.M is grateful for support from the Sloan Foundation and Research Corporation under the Cottrell Scholarship and Research Innovation programs.
Funders:
Funding AgencyGrant Number
NIHR01 GM66142-01
AstraZenecaUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
DuPontUNSPECIFIED
GlaxoSmithKlineUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
LillyUNSPECIFIED
MateriaUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
PfizerUNSPECIFIED
PharmaciaUNSPECIFIED
Roche BiosciencesUNSPECIFIED
Alfred P. Sloan FoundationUNSPECIFIED
Cottrell Scholar of Research CorporationUNSPECIFIED
Record Number:CaltechAUTHORS:20170417-065654426
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20170417-065654426
Official Citation:The First Enantioselective Organocatalytic Mukaiyama−Michael Reaction:  A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture Sean P. Brown, Nicole C. Goodwin, and David W. C. MacMillan Journal of the American Chemical Society 2003 125 (5), 1192-1194 DOI: 10.1021/ja029095q
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76582
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:17 Apr 2017 16:31
Last Modified:17 Apr 2017 16:31

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