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
Externally publishedYes

Fingerprint

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

All Science Journal Classification (ASJC) codes

  • 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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