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. 2010 Mar 10;132(9):2895-7.
doi: 10.1021/ja9109105.

Copper-catalyzed gamma-selective allyl-alkyl coupling between allylic phosphates and alkylboranes

Hirohisa Ohmiya  1 , Umi Yokobori, Yusuke Makida, Masaya Sawamura
Affiliations

Copper-catalyzed gamma-selective allyl-alkyl coupling between allylic phosphates and alkylboranes

Hirohisa Ohmiya et al. J Am Chem Soc. .

Abstract

Copper-catalyzed allyl-alkyl coupling between allylic phosphates and alkylboranes, prepared by hydroboration of alkenes with 9-BBN-H, takes place with complete gamma- 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.

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