Synthesis of Primary sec-alkylamines via nucleophilic ring-opening of N-phosphorylated aziridines

…, A Napieraj, K Osowska-Pacewicka, S Zawadzki…

Index: Gajda, Tadeusz; Napieraj, Anna; Osowska-Pacewicka, Krystyna; Zawadzki, Stefan; Zwierzak, Andrzej Tetrahedron, 1997 , vol. 53, # 13 p. 4935 - 4946

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Citation Number: 21

Abstract

The novel ring-opening reaction of various 2-alkyl-and 2, 2-dimethyl-N-(diethoxyphosphoryl) aziridines (1) and (10) with copper-modified Grignard reagents proceeds regiospecifically at the less hindered carbon. The diethyl N-sec-alkylphosphoramidates (2) thus obtained may efficiently be converted to primary sec-alkylamine hydrochlorides (3) by refluxing with 20% hydrochloric acid. 2, 3-Disubstituted N-phosphorylated aziridines except N- ...