Stereoselective Synthesis of Trisubstituted α,β-Unsaturated Esters and Amides via Reactions of Tantalum-Alkyne Complexes Derived from Acetylenic Esters and Amides with Carbonyl Compounds

Kazuhiko Takai, Makoto Tezuka, Kiitiro Utimoto

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Treatment of acetylenic esters with low-valent tantalum (TaCl5 and Zn) in DME and benzene produces tantalum-alkyne complexes (not isolated), which react with carbonyl compounds regioselectively at the α-position of the esters to give Z isomers of trisubstituted α,β-unsaturated esters in a stereoselective manner. In contrast, tantalum-alkyne complexes derived from acetylenic amides react with carbonyl compounds at the β-position of the amides predominantly.

Original languageEnglish
Pages (from-to)5980-5982
Number of pages3
JournalJournal of Organic Chemistry
Volume56
Issue number21
DOIs
Publication statusPublished - Oct 1 1991
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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