Lithiation of Allyl Chlorides and Reactions with Electrophiles.

Abstract Deprotonation of allyl chlorides 1 and 8 with lithium diisopropylamide (LDA) gives chlorocinnamyllithium 2 and benzothiazolylchloroallyllithium 9 . Both 2 and 9 react with unenolizable carbonyl compounds with the in situ quench procedure furnishing styryl oxiranes 7 and benzothiazolylvinyl oxiranes 10 . In the absence of an external electrophile, 2 undergoes a homocoupling reaction leading to the enyne 5 . Lithiation of 1 , followed by the addition of the carbonyl compound, provides propargylic alcohols 6 .