The magnitude of the stereodirecting effect of an allylic alkoxy-substituent in an amidomercuration cyclization

James M. Takacs, Mark A. Helle, Bharat J. Sanyal, Todd A. Eberspacher

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A surprisingly large stereodirecting effect for the allylic alkoxy-substituent (> 4 kcal/mol) is revealed in the amidomercuration cyclization of an unsaturated amidal in which the stereodirecting effect of the allylic alkoxy-substituent competes against the stcreodirecting effect of a stereogenic amidal center.

Original languageEnglish (US)
Pages (from-to)6765-6768
Number of pages4
JournalTetrahedron Letters
Volume31
Issue number47
DOIs
StatePublished - 1990

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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