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

In: Organic Letters, Vol. 4, No. 25, 12.12.2002, p. 4463-4466.

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

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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.",

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AU - Miura, Tomoya

AU - Kiyota, Koichi

AU - Kusama, Hiroyuki

AU - Lee, Kooyeon

AU - Lee, Phil Ho

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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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