Selective mono- and 1,2-difunctionalisation of cyclopentene derivatives via Mg and Cu intermediates.
Christina Despotopoulou, Richard C Bauer, Arkady Krasovskiy, Peter Mayer, Jeffrey M Stryker, Paul Knochel
文献索引:Chemistry 14 , 2499, (2008)
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摘要
A single Br/Mg exchange of 1,2-dibromocyclopentene with iPrMgCl LiCl provides the corresponding beta-bromocyclopentenylmagnesium reagent, which can then be reacted with various electrophiles (yields: 65-82 %). In the presence of a secondary alkylmagnesium halide and Li2CuCl4 (2 mol %), these 2-bromoalkenylmagnesium compounds undergo bromine substitution and can then further react with electrophiles to give 1,2-difunctionalised cyclopentenes (63-79 %). The mechanism of this process is discussed.
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2007-01-15
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