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Copper-Catalyzed γ-Selective Allyl−Alkyl Coupling between Allylic Phosphates and Alkylboranes

2010; American Chemical Society; Volume: 132; Issue: 9 Linguagem: Inglês

10.1021/ja9109105

1943-2984

Hirohisa Ohmiya, Umi Yokobori, Yusuke Makida, Masaya Sawamura,

Chemical Synthesis and Analysis

Copper-catalyzed allyl−alkyl coupling between allylic phosphates and alkylboranes, prepared by hydroboration of alkenes with 9-BBN-H, takes place with complete γ- and E-selectivities and with preferential 1,3-anti stereochemistry. The reaction tolerates various functional groups in both the allylic phosphate and alkylborane. Catalytic mechanisms involving transmetalation between a trialkyl(alkoxo)borate and a copper(I) complex to form an alkylcopper(I) species are proposed.