BENZOTRIAZOLE-ASSISTED BETA-LITHIATION OF VINYL ETHERS

Authors
KATRITZKY AR IGNATCHENKO AV LAN XF LANG HY STEVENS CV OPITZ A KOCH R ANDERS E
Citation
Ar. Katritzky et al., BENZOTRIAZOLE-ASSISTED BETA-LITHIATION OF VINYL ETHERS, Tetrahedron, 50(20), 1994, pp. 6005-6016
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
20
Year of publication
1994
Pages
6005 - 6016
Database
ISI
SICI code
0040-4020(1994)50:20<6005:BBOVE>2.0.ZU;2-3
Abstract
Benzotriazole-assisted beta-deprotonation of (alpha-benzotriazolylviny l) ethers occurs stereoselectively at the cis position as shown by que nching with a variety of electrophiles. Semiempirical calculations of the lithiated enol ethers by PM3 and MNDO methods disclosed a higher s tabilization for the cis-isomers over the corresponding trans-isomers.