Synlett 2014; 25(17): 2488-2492
DOI: 10.1055/s-0034-1379014
letter
© Georg Thieme Verlag Stuttgart · New York

An Improvement of the Palladium-Catalyzed [4+2] Cycloaddition of o-(Silylmethyl)benzyl Carbonates with Alkenes

Yushu Jin
a   Department of Chemistry, Graduate School of Sciences, and International Research Center for Molecular Systems (IRCMS), Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
,
Kentaro Ishizuka
b   Education Center for Global Leaders in Molecular Systems for Devices, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
,
Ryoichi Kuwano*
a   Department of Chemistry, Graduate School of Sciences, and International Research Center for Molecular Systems (IRCMS), Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
c   JST ACT-C, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan   Fax: +81(92)6422572   Email: rkuwano@chem.kyushu-univ.jp
› Author Affiliations
Further Information

Publication History

Received: 12 June 2014

Accepted after revision: 01 August 2014

Publication Date:
25 August 2014 (online)


Abstract

The palladium complex, which is generated in situ from Pd(η 3-C3H5)Cp and tris(4-methoxy-3,5-dimethylphenyl)phosphine, catalyzed the [4+2] cycloaddition of o-(silylmethyl)benzyl carbonates with alkenes. The reaction of the benzyl esters with methyl crotonate gave methyl 3-methyltetralin-2-carboxylate in 84% yield with 2% catalyst loading.

Supporting Information

 
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