Synlett 2002(5): 0755-0758
DOI: 10.1055/s-2002-25336
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Enantiopure 1-Benzyl-2,3-disubstituted Piperazines from Enantiopure p-Toluenesulfinimines

Alma Viso*a, Roberto Fernández de la Pradilla*a, María L. López-Rodríguezb, Ana Garcíaa, Mariola Tortosaa
a Instituto de Química Orgánica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain
b Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain
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Publication History

Received 7 February 2002
Publication Date:
07 February 2007 (online)


The treatment of enantiopure N-sulfinyl-N′-benzyldiaminoalcohols with diethyl oxalate and sodium methoxide followed by reduction with BH3 affords enantiopure 1-benzyl-2,3-disubstituted piperazines. A related sequence produces substituted monoketopiperazines in good yields.