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

doi:10.1021/ol2008507

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 journal › Article › peer-review

42 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 language	English
Pages (from-to)	2959-2961
Number of pages	3
Journal	Organic letters
Volume	13
Issue number	11
DOIs	https://doi.org/10.1021/ol2008507
Publication status	Published - Jun 3 2011
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol2008507

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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.",

author = "Yoichiro Kuninobu and Hironori Matsuzaki and Mitsumi Nishi and Kazuhiko Takai",

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T1 - Rhenium-catalyzed regio- and stereoselective addition of two carbon units to terminal alkynes via carbon-carbon bond cleavage of β-keto sulfones

AU - Kuninobu, Yoichiro

AU - Matsuzaki, Hironori

AU - Nishi, Mitsumi

AU - Takai, Kazuhiko

PY - 2011/6/3

Y1 - 2011/6/3

N2 - 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.

AB - 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.

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

Abstract

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