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
Publication statusPublished - 1991
Externally publishedYes

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Tantalum
Carbonyl compounds
Alkynes
Amides
Esters
Benzene
Isomers

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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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.",
author = "Kazuhiko Takai and Makoto Tezuka and Kiitiro Utimoto",
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journal = "Journal of Organic Chemistry",
issn = "0022-3263",
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T1 - 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

AU - Takai, Kazuhiko

AU - Tezuka, Makoto

AU - Utimoto, Kiitiro

PY - 1991

Y1 - 1991

N2 - 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.

AB - 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.

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