Rhenium-catalyzed regio- and stereoselective synthesis of γ-thio-α,β-unsaturated ketones via insertion of terminal alkynes into the C-S bond

Mitsumi Nishi, Yoichiro Kuninobu, Kazuhiko Takai

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The reaction of α-thioketones and alkynes in the presence of a rhenium catalyst, [HRe(CO)4]n, gave γ-thio-α, β-unsaturated ketones in excellent yields. The alkynes were inserted into the carbon-sulfur bond of the α-thioketones, and isomerization of a double bond provided the products with high regio- and stereoselectivities. This reaction also proceeded in an intramolecular fashion.

Original languageEnglish
Pages (from-to)6116-6118
Number of pages3
JournalOrganic Letters
Volume14
Issue number23
DOIs
Publication statusPublished - Dec 7 2012

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Rhenium
Alkynes
rhenium
alkynes
Ketones
ketones
insertion
Stereoselectivity
Regioselectivity
Carbon Monoxide
synthesis
Isomerization
Sulfur
isomerization
sulfur
Carbon
catalysts
Catalysts
carbon
products

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Rhenium-catalyzed regio- and stereoselective synthesis of γ-thio-α,β-unsaturated ketones via insertion of terminal alkynes into the C-S bond. / Nishi, Mitsumi; Kuninobu, Yoichiro; Takai, Kazuhiko.

In: Organic Letters, Vol. 14, No. 23, 07.12.2012, p. 6116-6118.

Research output: Contribution to journalArticle

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