Regioselective functionalization of 2-arylazetidines: evaluating the ortho-directing ability of the azetidinyl ring and the α-directing ability of the N-substituent†‡,10.1039/C3CC48555B

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Regioselective functionalization of 2-arylazetidines: evaluating the ortho-directing ability of the azetidinyl ring and the α-directing ability of the N-substituent†‡

Leonardo Degennaro,Marina Zenzola,Piera Trinchera,Laura Carroccia,Arianna Giovine,Giuseppe Romanazzi,Aurelia Falcicchio,Renzo Luisi

Chemical Communications Pub Date : 12/06/2013 00:00:00 , DOI:10.1039/C3CC48555B

Abstract

The regioselective lithiation–functionalization of 2-arylazetidines has been explored. The nature of the N-substituent is mainly responsible for a regioselectivity switch. ortho-Lithiation occurred, using hexyllithium as a greener base, in N-alkylazetidines, while α-benzylic lithiation has been observed with N-Boc azetidines.