Highly diastereoselective aldol additions of a chiral ethyl ketone enolate under Lewis base catalysis

Scott E Denmark, Son M. Pham

Research output: Contribution to journalArticlepeer-review

Abstract

(Matrix presented) The aldol addition of a chiral ethyl ketone enolate bearing an oxygen substituent (OTBS) at the α-position proceeds with high internal and relative diastereoselectivities with various achiral aldehydes in good yields. The profound influence of the resident stereogenic center allows for the use of an achiral catalyst, such as HMPA, with minor attenuation in internal stereoselectivity.

Original languageEnglish (US)
Pages (from-to)2201-2204
Number of pages4
JournalOrganic Letters
Volume3
Issue number14
DOIs
StatePublished - Jul 12 2001

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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