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

doi:10.1021/ol302810u

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 journal › Article › peer-review

12 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 language	English
Pages (from-to)	6116-6118
Number of pages	3
Journal	Organic Letters
Volume	14
Issue number	23
DOIs	https://doi.org/10.1021/ol302810u
Publication status	Published - Dec 7 2012

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol302810u

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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.",

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T1 - Rhenium-catalyzed regio- and stereoselective synthesis of γ-thio-α,β-unsaturated ketones via insertion of terminal alkynes into the C-S bond

AU - Nishi, Mitsumi

AU - Kuninobu, Yoichiro

AU - Takai, Kazuhiko

PY - 2012/12/7

Y1 - 2012/12/7

N2 - 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.

AB - 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.

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JF - Organic Letters

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ER -

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

Abstract

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