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. 2002 Jun 19;124(24):6798-9.
doi: 10.1021/ja0262378.

The first direct and enantioselective cross-aldol reaction of aldehydes

Alan B Northrup  1 , David W C MacMillan
Affiliations
Free article

The first direct and enantioselective cross-aldol reaction of aldehydes

Alan B Northrup et al. J Am Chem Soc. .
Free article

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 (R1 = Me, n-Bu, Bn, 91 to >99%) and aldol acceptor (R2 = 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 beta-hydroxy aldehydes which are valuable intermediates in polyketide syntheses.

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