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

DOI: 10.1021/ol0362865

Source and publish data:

Organic Letters p. 529 - 531 (2004)

Update date:2022-08-05

Topics:

Authors:

Calaza, M. Isabel

Yang, Xiaoyin

Soorukram, Darunee

Knochel, Paul

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Article abstract of DOI:10.1021/ol0362865

(Equation presented) 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 S_N2 selectivity. The addition of ZnBr₂ changes this selectivity and allows the performance of highly regioselective and enantioselective anti S _N2′ substitutions using open-chain allylic pentafluorobenzoates.

Full text of DOI:10.1021/ol0362865

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