Selective Mono??and 1, 2??Difunctionalisation of Cyclopentene Derivatives via Mg and Cu Intermediates

…, A Krasovskiy, P Mayer, JM Stryker…

Index: Despotopoulou, Christina; Bauer, Richard C.; Krasovskiy, Arkady; Mayer, Peter; Stryker, Jeffrey M.; Knochel, Paul Chemistry - A European Journal, 2008 , vol. 14, # 8 p. 2499 - 2506

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Citation Number: 23

Abstract

Abstract A single Br/Mg exchange of 1, 2-dibromocyclopentene with iPrMgCl⋅ LiCl provides the corresponding β-bromocyclopentenylmagnesium reagent, which can then be reacted with various electrophiles (yields: 65–82%). In the presence of a secondary alkylmagnesium halide and Li 2 CuCl 4 (2 mol%), these 2-bromoalkenylmagnesium compounds undergo bromine substitution and can then further react with electrophiles to give 1, 2- ...