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Stereoselective SN2-Substitutions Using Polyfunctional Lithium Arylcuprates Prepared by an Iodine−Copper Exchange

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journal contribution
posted on 19.02.2004, 00:00 by M. Isabel Calaza, Xiaoyin Yang, Darunee Soorukram, Paul Knochel
Polyfunctional mixed lithium arylcuprates of the type (FG-Ar)(PhMe2CCH2)CuLi obtained via iodine− or bromine−copper exchange with (PhMe2CCH2)2CuLi react with cyclic 2-iodoallylic acetates with high SN2 selectivity. The addition of ZnBr2 changes this selectivity and allows the performance of highly regioselective and enantioselective anti SN2‘ substitutions using open-chain allylic pentafluorobenzoates.