Abstract

The S N 2'-selective reaction of organocopper or organozinc reagents with allylic chlorides having a chiral center at the 6-position proceeds with up to 100% diastereoselectivity. The observed 1,2-asymmetric induction conforms to pure steric control (Cram-Felkin-Anh model) even in cases where conventional chelation control may seen 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 a-substituted carbonyl compounds

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