1,2-Asymmetric Induction in the SN2'-Allylation of Organocopper and Organozinc Reagents

Article abstract of DOI:10.1021/jo00071a022

The S_N2'-selective reaction of organocopper or organizinc reagents with allylic chlorides having a chiral center at the δ-position proceeds with up to 100percent diastereoselectivity.The observed 1,2-asymmetric induction conforms to pure steric control (Cram-Felkin-Anh model) even in cases where conventional chelation control may seem to operate, and the level of the selectivity was found to be much higher than those found for the additions of organometallics to structurally comparable α-substituted carbonyl compounds.