Stereoselective S N 2-substitutions using polyfunctional lithium arylcuprates prepared by an iodine-copper exchange |
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| Authors: | Calaza M Isabel Yang Xiaoyin Soorukram Darunee Knochel Paul |
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| Affiliation: | Department Chemie, Ludwig-Maximilians-Universit?t, Butenandtstrasse 5-13, 81377, München, Germany. |
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| Abstract: | [reaction: see text] Polyfunctional mixed lithium arylcuprates of the type (FG-Ar)(PhMe(2)CCH(2))CuLi obtained via iodine- or bromine-copper exchange with (PhMe(2)CCH(2))(2)CuLi react with cyclic 2-iodoallylic acetates with high S(N)2 selectivity. The addition of ZnBr(2) changes this selectivity and allows the performance of highly regioselective and enantioselective anti S(N)2' substitutions using open-chain allylic pentafluorobenzoates. |
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