Diastereoselective aldol additions of chiral β-hydroxy ethyl ketone enolates catalyzed by Lewis bases

Scott E. Denmark, Shinji Fujimori

Research output: Contribution to journalArticlepeer-review

Abstract

(matrix presented) The trichlorosilyl enolates derived from chiral ethyl ketones bearing a β-hydroxyl group and an α-stereogenic center were employed in the phosphoramide-catalyzed aldol reaction. The addition of Z-enolates to achiral aldehydes produced aldol products in good yields and high syn relative diastereoselectivities. The internal diastereoselectivity is controlled by the catalyst configuration, allowing for selective formation of either syn diastereomer.

Original languageEnglish (US)
Pages (from-to)3473-3476
Number of pages4
JournalOrganic Letters
Volume4
Issue number20
DOIs
StatePublished - Oct 3 2002

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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