Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents

Shermin S Goh, Sureshbabu Guduguntla, Takashi Kikuchi, Martin Lutz, Edwin Otten, Makoto Fujita, Ben L Feringa

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Abstract

The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The cycloheptene products undergo an unusual ring contraction. The synthetic versatility of this Cu(I)-catalyzed reaction is demonstrated by the concise stereocontrolled preparation of cyclic amino alcohols, which are privileged chiral structures in natural products and pharmaceuticals and widely used in synthesis and catalysis.

Original languageEnglish
Pages (from-to)7052-7055
Number of pages4
JournalJournal of the American Chemical Society
Volume140
Issue number23
DOIs
Publication statusPublished - 13-Jun-2018

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