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Published June 19, 2002 | Supplemental Material
Journal Article Open

The First Direct and Enantioselective Cross-Aldol Reaction of Aldehydes


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.

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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August 19, 2023
October 25, 2023