Cyclization by intramolecular carbolithiation of alkyl-and vinyllithiums prepared by reductive lithiation: Surprising stereochemistry in the lithium oxyanion accelerated …

K Deng, A Bensari, T Cohen

Index: Deng, Kai; Bensari, Ahlem; Cohen, Theodore Journal of the American Chemical Society, 2002 , vol. 124, # 41 p. 12106 - 12107

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Citation Number: 42

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 reductive lithiation allows virtually any kind of organolithium to be generated, ...