title: Stereoselective functionalization of cyclopropane derivatives using bromine/magnesium and sulfoxide/magnesium exchange reactions.
abstract: The reaction of 2,2-dibromo-1-methyl-cyclopropanecarbonitrile (1) with i-PrMgCl in Et(2)O/CH(2)Cl(2) provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved. [reaction: see text]
authors.affiliation: Department Chemie und Biochemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, 81377 Munich, Germany.
authors.forename: Felix
authors.initials: F
authors.lastname: Kopp
authors.forename: Genia
authors.initials: G
authors.lastname: Sklute
authors.forename: Kurt
authors.initials: K
authors.lastname: Polborn
authors.forename: Ilan
authors.initials: I
authors.lastname: Marek
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel