Synlett 2014; 25(16): 2281-2284
DOI: 10.1055/s-0034-1378371
cluster
© Georg Thieme Verlag Stuttgart · New York

Regio- and Diastereoselective Nickel-Catalyzed Cycloaddition of Activated Cyclopropanes with Allenes

Rihoko Tombe
a  Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan   Fax: +81(75)3832438   Email: kurahashi.takuya.2c@kyoto-u.ac.jp   Email: matsubara.seijiro.2e@kyoto-u.ac.jp
,
Takahiro Iwamoto
a  Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan   Fax: +81(75)3832438   Email: kurahashi.takuya.2c@kyoto-u.ac.jp   Email: matsubara.seijiro.2e@kyoto-u.ac.jp
,
Takuya Kurahashi*
a  Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan   Fax: +81(75)3832438   Email: kurahashi.takuya.2c@kyoto-u.ac.jp   Email: matsubara.seijiro.2e@kyoto-u.ac.jp
b  JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan
,
Seijiro Matsubara*
a  Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan   Fax: +81(75)3832438   Email: kurahashi.takuya.2c@kyoto-u.ac.jp   Email: matsubara.seijiro.2e@kyoto-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 14 May 2014

Accepted after revision: 11 June 2014

Publication Date:
06 August 2014 (online)


Abstract

Nickel-catalyzed intermolecular [3+2] cycloaddition of activated cyclopropanes with allenes has been developed. This transformation generates highly substituted five-membered carbocyclic compounds with good regio- and diastereoselectivity under mild reaction conditions. This reaction can be extended to a broad variety of allenes to obtain the corresponding adducts.

Supporting Information

 
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