STEREOSPECIFIC SYNTHESIS OF 1-ALKYLIMIDAZOLE DERIVATIVES VIA MITSUNOBU REACTIONS

Authors
BOTTA M SUMMA V TRAPASSI G MONTEAGUDO E CORELLI F
Citation
M. Botta et al., STEREOSPECIFIC SYNTHESIS OF 1-ALKYLIMIDAZOLE DERIVATIVES VIA MITSUNOBU REACTIONS, Tetrahedron : asymmetry, 5(2), 1994, pp. 181-184
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
2
Year of publication
1994
Pages
181 - 184
Database
ISI
SICI code
0957-4166(1994)5:2<181:SSO1DV>2.0.ZU;2-H
Abstract
4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alc ohols 1 under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazol e derivatives 2, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 4 in good overall yield and hi gh enantiomeric excess. The absolute stereochemistry of the compounds has been confirmed by synthesizing 4c through an independent route.