A silicon-position dependent 6-endo-trig cyclization during Tsuji-Trost alkylation

TETRAHEDRON

卷:69

Article

Agarwal, Jyoti¹  Commandeur, Claude¹  Malacria, Max¹  Thorimbert, Serge¹ 

[1] UPMC Sorbonne Univ, Inst Parisien Chim Mol, UMR CNRS 7201, F-75005 Paris, France

关键词: Tsuji-Trost alkylation;    Cyclization;    Palladium;    Regioselectivity;    Silicon derivatives;   

DOI  :  10.1016/j.tet.2013.08.080

来源: Elsevier

【 摘 要 】

Two silylated cyclohexenes products have been prepared by using a Tsuji-Trost palladium-catalyzed cyclization. It involves the generation of a cationic pi-allylic palladium complex bearing a triethylsilyl group on C-3, which cyclizes via a 6-endo-trig process to afford the cyclohexene derivatives. It is also demonstrated that the position of the silyl group on the starting allylic substrate strongly influenced the reaction. It could favor either the production of the expected cyclohexenyl ring or a diene by an elimination that occurs on the silyl-substituted C-2 pi-allylic palladium complex. (C) 2013 Elsevier Ltd. All rights reserved.

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