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The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes

Northrup, Alan B. and MacMillan, David W. C. (2002) The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes. Journal of the American Chemical Society, 124 (24). pp. 6798-6799. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170426-154358045

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Abstract

The first enantioselective catalytic direct cross-aldol reaction that employs nonequivalent aldehydes has been accomplished using proline as the reaction catalyst. Structural variation in both the aldol donor (R_1 = Me, n-Bu, Bn, 91 to >99%) and aldol acceptor (R_2 = I-Pr, I-Bu, c-C6H11, Et, Ph, 97−99% ee) are possible while maintaining high reaction efficiency (75−88% yield). Significantly, this new aldol variant allows facile enantioselective access to a broad range of β-hydroxy aldehydes which are valuable intermediates in polyketide syntheses.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja0262378DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja0262378PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja0262378PublisherSupporting Information
Additional Information:© 2002 American Chemical Society. Received March 19, 2002. Publication Date (Web): May 8, 2002. We thank S. P. Brown, N. C. Goodwin, and I. K. Mangion for early contributions to this work. Financial support was provided by AstraZeneca, GlaxoSmithKline, Johnson and Johnson, Lilly, Merck Research Laboratories, and Pfizer. A.B.N. is grateful for an NSF predoctoral fellowship.
Funders:
Funding AgencyGrant Number
AstraZenecaUNSPECIFIED
GlaxoSmithKlinUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
LillyUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
PfizerUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:24
Record Number:CaltechAUTHORS:20170426-154358045
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170426-154358045
Official Citation:The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes Alan B. Northrup and David W. C. MacMillan Journal of the American Chemical Society 2002 124 (24), 6798-6799 DOI: 10.1021/ja0262378
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76965
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:26 Apr 2017 22:59
Last Modified:03 Oct 2019 17:51

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