A removable auxiliary for amidomercuration reactions: The stereocontrolled preparation of vicinal aminoalcohols

James M. Takacs, Mark A. Helle, Linrong Yang

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Unsaturated amidals 1, derived from allylic alcohols and containing a stereogenic amidal center, undergo amidomercuration with high 1,3-stereoinduction from the amidal center. In substrates derived from secondary allylic alcohols, the influence of the stereogenic amidal center overrides the competing 1,2-stereoinduction from the allylic substituent. Consequently, starting from a single secondary allylic alcohol, the amidal auxiliary enables the selective preparation of either a syn or an anti vicinal aminoalcohol.

Original languageEnglish (US)
Pages (from-to)1777-1780
Number of pages4
JournalTetrahedron Letters
Volume30
Issue number14
DOIs
StatePublished - 1989

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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