Synthesis of 4, 4-Disubstituted β-Lactams by Regiospecific Electrophile-and Silver-Induced Ring Expansion of 2, 2-Disubstituted 1-Methoxycyclopropylamines

N De Kimpe, K Abbaspour Tehrani…

Index: De Kimpe, Norbert; Tehrani, Kourosch Abbaspour; Fonck, Gwendolien Journal of Organic Chemistry, 1996 , vol. 61, # 19 p. 6500 - 6503

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Citation Number: 29

Abstract

2, 2-Disubstituted 1-methoxycyclopropylamines underwent regiospecific ring expansion to 1, 4, 4-trisubstituted 2-azetidinones by N-chlorination with tert-butyl hypochlorite and subsequent rearrangement with silver tetrafluoroborate. Upon thermolysis, 4, 4-disubstituted β-lactams suffer a characteristic ring opening to afford β, γ-unsaturated carboxylic amides. The reduction of 1, 4, 4-trisubstituted 2-azetidinones with lithium aluminum hydride ...