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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 and Ben L. Feringa*

*Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Email: b.l.feringarug.nl

S. S. Goh, S. Guduguntly, T. Kikuchi, M. Lutz, E. Otten, M. Fujita, B. L. Feringa, J. Am. Chem. Soc., 2018, 140, 7052-7055.

DOI: 10.1021/jacs.8b02992 (free Supporting Information)


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Abstract

Asymmetric allylic substitution with organolithium reagents enables a highly regio- and enantioselective desymmetrization of meso-1,4-dibromocycloalk-2-enes to afford enantioenriched bromocycloalkenes. The cycloheptene products undergo an unusual ring contraction.

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Key Words

cyclopentenes, cyclohexenes, allylation


ID: J48-Y2018