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.feringa
rug.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
see article for more reactions
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.
see article for more examples
Key Words
cyclopentenes, cyclohexenes, allylation
ID: J48-Y2018
