Rhenium-catalyzed regio- and stereoselective addition of two carbon units to terminal alkynes via carbon-carbon bond cleavage of β-keto sulfones

Yoichiro Kuninobu, Hironori Matsuzaki, Mitsumi Nishi, Kazuhiko Takai

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Treatment of β-keto sulfones with terminal alkynes gave unsaturated δ-keto sulfones in good to excellent yields under rhenium catalysis. In this reaction, the insertion of the alkynes into the nonstrained carbon-carbon single bond between the α- and β-positions of the β-keto sulfones proceeded smoothly, and (Z)-isomers were produced with high regio- and stereoselectivities.

Original languageEnglish
Pages (from-to)2959-2961
Number of pages3
JournalOrganic Letters
Volume13
Issue number11
DOIs
Publication statusPublished - Jun 3 2011

Fingerprint

Rhenium
Sulfones
sulfones
Alkynes
rhenium
alkynes
cleavage
Carbon
carbon
Stereoselectivity
Regioselectivity
Catalysis
Isomers
catalysis
insertion
isomers

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Rhenium-catalyzed regio- and stereoselective addition of two carbon units to terminal alkynes via carbon-carbon bond cleavage of β-keto sulfones. / Kuninobu, Yoichiro; Matsuzaki, Hironori; Nishi, Mitsumi; Takai, Kazuhiko.

In: Organic Letters, Vol. 13, No. 11, 03.06.2011, p. 2959-2961.

Research output: Contribution to journalArticle

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