Tetrahedron

Synthesis of enantiopure 1-substituted, 1, 2-disubstituted, and 1, 4, 5-trisubstituted imidazoles from 1, 2-amino alcohols

Y Matsuoka, Y Ishida, D Sasaki, K Saigo

Index: Matsuoka, Yuki; Ishida, Yasuhiro; Sasaki, Daisuke; Saigo, Kazuhiko Tetrahedron, 2006 , vol. 62, # 34 p. 8199 - 8206

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Citation Number: 36

Abstract

Synthetic strategies for the preparation of imidazoles with a stereogenic N-substituent are classified into two categories; (i) the alkylation of an imidazole nitrogen with enantiopure electrophiles and (ii) the cyclocondensation of ring fragments, typically the combination of glyoxal, ammonia, an aldehyde, and an enantiopure primary amine. The alkylation method is quite straightforward to access target molecules, because imidazole is commercially available and the N- ...

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