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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.

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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.

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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.
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Johnson and JohnsonUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:24
Record Number:CaltechAUTHORS:20170426-154358045
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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
Deposited By: Tony Diaz
Deposited On:26 Apr 2017 22:59
Last Modified:03 Oct 2019 17:51

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