Elsevier

Tetrahedron

Volume 50, Issue 20, 1994, Pages 6005-6016
Tetrahedron

Benzotriazole-assisted β-lithiation of vinyl ethers

https://doi.org/10.1016/S0040-4020(01)90453-3Get rights and content

Abstract

Benzotriazole-assisted β-deprotonation of (α-benzotriazolylvinyl) ethers occurs stereoselectively at the cis position as shown by quenching with a variety of electrophiles. Semiempirical calculations of the lithiated enol ethers by PM3 and MNDO methods disclosed a higher stabilization for the cis-isomers over the corresponding trans-isomers.

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