Highly enantioselective phase-transfer-catalyzed alkylation of protected α-amino acid amides toward practical asymmetric synthesis of vicinal diamines, α-amino …

…, D Kato, Y Uematsu, E Tayama, D Sakai…

Index: Ooi, Takashi; Takeuchi, Mifune; Kato, Daisuke; Uematsu, Yukitaka; Tayama, Eiji; Sakai, Daiki; Maruoka, Keiji Journal of the American Chemical Society, 2005 , vol. 127, # 14 p. 5073 - 5083

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Citation Number: 44

Abstract

Highly enantioselective alkylation of protected glycine diphenylmethyl (Dpm) amide 1 and Weinreb amide 10 has been realized under phase-transfer conditions by the successful utilization of designer chiral quaternary ammonium salts of type 4 as catalyst. Particularly, remarkable reactivity of the chiral ammonium enolate derived from 1b and 4c allowed the reaction with less reactive simple secondary alkyl halides with high efficiency and ...