The first direct and enantioselective cross-aldol reaction of aldehydes

Alan B. Northrup, David W.C. MacMillan

Research output: Contribution to journalArticle

642 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 languageEnglish (US)
Pages (from-to)6798-6799
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number24
DOIs
StatePublished - Jun 19 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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