The first direct and enantioselective cross-aldol reaction of aldehydes

Alan B. Northrup; David W.C. MacMillan

doi:10.1021/ja0262378

The first direct and enantioselective cross-aldol reaction of aldehydes

Alan B. Northrup, David W.C. MacMillan

Research output: Contribution to journal › Article › peer-review

737 Scopus citations

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 β-hydroxy aldehydes which are valuable intermediates in polyketide syntheses.

Original language	English (US)
Pages (from-to)	6798-6799
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	124
Issue number	24
DOIs	https://doi.org/10.1021/ja0262378
State	Published - Jun 19 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja0262378

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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 (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 β-hydroxy aldehydes which are valuable intermediates in polyketide syntheses.",

author = "Northrup, \{Alan B.\} and MacMillan, \{David W.C.\}",

year = "2002",

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AB - 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 β-hydroxy aldehydes which are valuable intermediates in polyketide syntheses.

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The first direct and enantioselective cross-aldol reaction of aldehydes

Abstract

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