Chiral benzimidazoles as hydrogen bonding organocatalysts

TETRAHEDRON LETTERS

卷:56

Article

Najera, Carmen¹ 

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

关键词: Enantioselective organocatalysis;    Benzimidazole;    Hydrogen bonding;    Michael reaction;    Nucleophilic substitution;    Aldol reaction;   

DOI  :  10.1016/j.tetlet.2015.03.099

来源: Elsevier

【 摘 要 】

Several bifunctional organocatalysts bearing the benzimidazole unit have been designed in order to act as bifunctional systems by hydrogen bonding. Chiral 2-aminobenzimidazoles are conformational rigid guanidines able to catalyze enantioselectively Michael reaction, direct S(N)1 of alcohols, and aldol reactions. Some of these organocatalysts can be easily recovered by simple isolation methods and reused without loss of catalytic activity. Related (2-aminoalkyl)benzimidazoles have been used as chiral organocatalysts in aldol and amination reactions of carbonyl compounds. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

Free