title: Highly anti-selective SN2' substitutions of chiral cyclic 2-iodo-allylic alcohol derivatives with mixed zinc-copper reagents.
abstract: [reaction: see text] Functionalized allylic electrophilic reagents such as chiral 2-iodo-1-cyclohexenyl and -cyclopentenyl phosphates undergo highly stereoselective anti-S(N)2'-allylic substitution reactions with a wide range of organozinc reagents (R(2)Zn and RZnI) leading to chiral products with a transfer of the chiral information >95%. The use of functionalized organozinc iodides allows preparation of the bicyclic enones 8 and 9 in >or=93% ee.
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, 81377 München, Germany.
authors.forename: M Isabel
authors.initials: MI
authors.lastname: Calaza
authors.forename: Eike
authors.initials: E
authors.lastname: Hupe
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel