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ChemInform Abstract: Enantioselective Carbolithiation of Cinnamyl Acetals. New Access to Chiral Disubstituted Cyclopropanes.

✍ Scribed by S. NORSIKIAN; I. MAREK; J.-F. POISSON; J. F. NORMANT

Publisher: John Wiley and Sons
Year: 2010
Weight: 28 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199752037

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✦ Synopsis

Enantioselective Carbolithiation of Cinnamyl Acetals. New Access to Chiral Disubstituted Cyclopropanes. -The use of the dimethyl acetal (I) allows a high enantioselective alkylation in the presence of a catalytic amount of (-)-sparteine to give after hydrolysis and deprotection alkylated alcohols (III). If the reaction mixture is warmed to room temperature, the primarily formed benzylic organolithium intermediate undergoes an internal nucleophilic substitution and a 1,3-elimination to give the title cyclopropanes (IV) with high enantioselectivity.

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