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 journalArticle

13 Citations (Scopus)

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

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Amiloride
Cyclization
alkoxyl radical

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

The magnitude of the stereodirecting effect of an allylic alkoxy-substituent in an amidomercuration cyclization. / Takacs, James M.; Helle, Mark A.; Sanyal, Bharat J.; Eberspacher, Todd A.

In: Tetrahedron Letters, Vol. 31, No. 47, 1990, p. 6765-6768.

Research output: Contribution to journalArticle

Takacs, James M. ; Helle, Mark A. ; Sanyal, Bharat J. ; Eberspacher, Todd A. / The magnitude of the stereodirecting effect of an allylic alkoxy-substituent in an amidomercuration cyclization. In: Tetrahedron Letters. 1990 ; Vol. 31, No. 47. pp. 6765-6768.
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