Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic β-keto esters with terminal alkynes

Yoichiro Kuninobu; Junya Morita; Mitsumi Nishi; Atsushi Kawata; Kazuhiko Takai

doi:10.1021/ol900772h

Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic β-keto esters with terminal alkynes

Yoichiro Kuninobu, Junya Morita, Mitsumi Nishi, Atsushi Kawata, Kazuhiko Takai

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

Treatment of cyclic βKeto esters with terminal alkynes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)₃(thf)] ₂, gave bicyclo[3.3.1]nonene derivatives. The reaction conditions and yields of the bicyclo[3.3.1]nonenes were improved by the sequential use of tetrabutylammonium fluoride (TBAF) after the rhenium-catalyzed reactions.

Original language	English
Pages (from-to)	2535-2537
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	12
DOIs	https://doi.org/10.1021/ol900772h
Publication status	Published - Jun 18 2009
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol900772h

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abstract = "Treatment of cyclic βKeto esters with terminal alkynes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)3(thf)] 2, gave bicyclo[3.3.1]nonene derivatives. The reaction conditions and yields of the bicyclo[3.3.1]nonenes were improved by the sequential use of tetrabutylammonium fluoride (TBAF) after the rhenium-catalyzed reactions.",

author = "Yoichiro Kuninobu and Junya Morita and Mitsumi Nishi and Atsushi Kawata and Kazuhiko Takai",

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AU - Kuninobu, Yoichiro

AU - Morita, Junya

AU - Nishi, Mitsumi

AU - Kawata, Atsushi

AU - Takai, Kazuhiko

PY - 2009/6/18

Y1 - 2009/6/18

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AB - Treatment of cyclic βKeto esters with terminal alkynes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)3(thf)] 2, gave bicyclo[3.3.1]nonene derivatives. The reaction conditions and yields of the bicyclo[3.3.1]nonenes were improved by the sequential use of tetrabutylammonium fluoride (TBAF) after the rhenium-catalyzed reactions.

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Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic β-keto esters with terminal alkynes

Abstract

ASJC Scopus subject areas

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