Investigation of Functionalized α??Chloroalkyllithiums for a Stereospecific Reagent??Controlled Homologation Approach to the Analgesic Alkaloid (−)??Epibatidine

…, LN Zakharov, PR Blakemore

Index: Emerson, Christopher R.; Zakharov, Lev N.; Blakemore, Paul R. Chemistry - A European Journal, 2013 , vol. 19, # 48 p. 16342 - 16356

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Citation Number: 14

Abstract

Abstract Four putative functionalized α-chloroakyllithiums RCH 2 CHLiCl, where R= CHCH 2 (18 a), CCH (18 b), CH 2 OBn (18 c), and CH [O (CH 2) 2 O](18 d), were generated in situ by sulfoxide–lithium exchange from α-chlorosulfoxides, and investigated for the stereospecific reagent-controlled homologation (StReCH) of phenethyl and 2-chloropyrid-5-yl (17) pinacol boronic esters. Deuterium labeling experiments revealed that α-chloroalkyllithiums are ...