Cyclization by intramolecular carbolithiation of alkyl- and vinyllithiums prepared by reductive lithiation: surprising stereochemistry in the lithium oxyanion accelerated cyclization.

Abstract

The versatility of intramolecular carbolithiation of simple alkenes to yield cyclopentylmethyllithiums by unconjugated organolithiums is greatly increased (1) by generating the organolithiums by reductive lithiation of phenyl thioethers with aromatic radical anions and (2) by using allylic or homoallylic alcohol groups on the receiving alkene. This type of… (More)

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