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Synthesis of (e)-vinylic tellurides and their transformation into α,β-unsaturated esters and carboxylic acids

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
36
Issue
42
Identifiers
DOI: 10.1016/0040-4039(95)01585-6
Disciplines
  • Chemistry

Abstract

Abstract Zirconum alkenyls and dienyls of E configuration obtained by the hydrozirconation of alkynes of conjugated enynes containing a terminal triple bond undergo the Zr Te exchange reaction by treatment with C 4H 9TeBr or C 4H 9Tel in THF at −78 °C. The Zr Te exchange reaction proceeds with total retention of configuration and with complete stereoselectivity at the carbon 1, furnishing ( E)-butyltelluro alkenes (64 - 86% yields) and ( E)-1-butylteluro-1,3-dienes (68 – 75%, yields) Vinylic tellurides were transformed into α,β-unsaturated esters and carboxylic acids with total retention of the regio- and stereochemistry via vtnyl lithium intermediates

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