An Efficient Method for Cyclopentene Annulation onto α,β-Unsaturated Ketones: W(CO)5(L)-Catalyzed 5-Endo-Dig Cyclization of 6-Siloxy-5-en-1-ynes

Nobuharu Iwasawa; Tomoya Miura; Koichi Kiyota; Hiroyuki Kusama; Kooyeon Lee; Phil Ho Lee

doi:10.1021/ol026993i

An Efficient Method for Cyclopentene Annulation onto α,β-Unsaturated Ketones: W(CO)₅(L)-Catalyzed 5-Endo-Dig Cyclization of 6-Siloxy-5-en-1-ynes

Nobuharu Iwasawa, Tomoya Miura, Koichi Kiyota, Hiroyuki Kusama, Kooyeon Lee, Phil Ho Lee

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

89 Citations (Scopus)

Abstract

(Matrix Presented) A highly efficient method for the cyclopentene annulation onto α,β-unsaturated ketones is described. Indium-mediated 1,4-propargylation onto α,β-unsaturated ketones in the presence of tert-butyldimethylsilyl triflate and dimethyl sulfide gives the 6-siloxy-5-en-1-yne derivatives, which undergo W(CO)₅(L)-catalyzed 5-endo-dig cyclization to give the corresponding cyclopentene derivatives in good yield.

Original language	English
Pages (from-to)	4463-4466
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	25
DOIs	https://doi.org/10.1021/ol026993i
Publication status	Published - Dec 12 2002
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "An Efficient Method for Cyclopentene Annulation onto α,β-Unsaturated Ketones: W(CO)5(L)-Catalyzed 5-Endo-Dig Cyclization of 6-Siloxy-5-en-1-ynes",

abstract = "(Matrix Presented) A highly efficient method for the cyclopentene annulation onto α,β-unsaturated ketones is described. Indium-mediated 1,4-propargylation onto α,β-unsaturated ketones in the presence of tert-butyldimethylsilyl triflate and dimethyl sulfide gives the 6-siloxy-5-en-1-yne derivatives, which undergo W(CO)5(L)-catalyzed 5-endo-dig cyclization to give the corresponding cyclopentene derivatives in good yield.",

author = "Nobuharu Iwasawa and Tomoya Miura and Koichi Kiyota and Hiroyuki Kusama and Kooyeon Lee and Lee, {Phil Ho}",

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T1 - An Efficient Method for Cyclopentene Annulation onto α,β-Unsaturated Ketones

T2 - W(CO)5(L)-Catalyzed 5-Endo-Dig Cyclization of 6-Siloxy-5-en-1-ynes

AU - Iwasawa, Nobuharu

AU - Miura, Tomoya

AU - Kiyota, Koichi

AU - Kusama, Hiroyuki

AU - Lee, Kooyeon

AU - Lee, Phil Ho

PY - 2002/12/12

Y1 - 2002/12/12

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AB - (Matrix Presented) A highly efficient method for the cyclopentene annulation onto α,β-unsaturated ketones is described. Indium-mediated 1,4-propargylation onto α,β-unsaturated ketones in the presence of tert-butyldimethylsilyl triflate and dimethyl sulfide gives the 6-siloxy-5-en-1-yne derivatives, which undergo W(CO)5(L)-catalyzed 5-endo-dig cyclization to give the corresponding cyclopentene derivatives in good yield.

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An Efficient Method for Cyclopentene Annulation onto α,β-Unsaturated Ketones: W(CO)₅(L)-Catalyzed 5-Endo-Dig Cyclization of 6-Siloxy-5-en-1-ynes

Abstract

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