The effects of a remote stereogenic center in the Lewis base catalyzed aldol additions of chiral trichlorosilyl enolates

Scott E. Denmark, Shinji Fujimori

Research output: Contribution to journalArticle

Abstract

(matrix presented) Chiral trichlorosilyl enolates bearing a remote stereogenic center were employed in the phosphoramide-catalyzed aldol reaction. The additions of the methyl ketone enolates proceeded with only moderate diastereoselectivities. The addition of the Z-enolate to various aldehydes selectively produced the syn relative diastereomers. In both cases, the effect of the β-silyloxy stereogenic center was modest, and the internal diastereoselection was mainly controlled by the catalyst.

Original languageEnglish (US)
Pages (from-to)3477-3480
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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