α-Substituent effect on olefination of ester carbonyl groups with ynolates

Satoshi Umezu, Mitsuru Shindo

Research output: Contribution to journalArticle

Abstract

In the olefination reaction of ester carbonyl with ynolate, an α-hetero (N, O, S)-substituent on the substrates was found to markedly improve the yields of tetrasubstituted olefins, even though it was sterically hindered. The α-substituent effect may be due to several factors including the addition based on the polar Felkin-Anh model and restricted conformation of the initial adducts.

Original languageEnglish
JournalTetrahedron Letters
Volume54
Issue number50
DOIs
Publication statusPublished - Aug 17 2013

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Alkenes
Conformations
Esters
Substrates

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

α-Substituent effect on olefination of ester carbonyl groups with ynolates. / Umezu, Satoshi; Shindo, Mitsuru.

In: Tetrahedron Letters, Vol. 54, No. 50, 17.08.2013.

Research output: Contribution to journalArticle

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