Chiral azole derivatives. 2. Synthesis of enantiomerically pure 1-alkylimidazoles

…, V Summa, A Brogi, E Monteagudo…

Index: Corelli; Summa; Brogi; Monteagudo; Botta Journal of Organic Chemistry, 1995 , vol. 60, # 7 p. 2008 - 2015

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Citation Number: 39

Abstract

4, 5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1- 7 in Table 1) under Mitsunobu conditions to give l-alkyl-4, 5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1- alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benzhydryl alcohols (entries 8-15), this sequence afforded the final ...