Synlett 2015; 26(01): 123-126
DOI: 10.1055/s-0034-1379489
letter
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Organocatalyzed Desymmetrization of 3-Substituted Cyclobutanones through Michael Addition to Nitroalkenes

Francesca Capitta
a   Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042 Monserrato (Cagliari), Italy   Email: fsecci@unica.it
b   CP3A Organic Synthesis Group, Institut de Chimie Moléculaire et des Matériaux d’Orsay – ICMMO (CNRS UMR 8182), Université Paris-Sud, 15 rue Georges Clémenceau, 91405 Orsay cedex, France   Fax: +39(70)6754388
,
Angelo Frongia
a   Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042 Monserrato (Cagliari), Italy   Email: fsecci@unica.it
,
Jean Ollivier*
b   CP3A Organic Synthesis Group, Institut de Chimie Moléculaire et des Matériaux d’Orsay – ICMMO (CNRS UMR 8182), Université Paris-Sud, 15 rue Georges Clémenceau, 91405 Orsay cedex, France   Fax: +39(70)6754388
,
David J. Aitken
b   CP3A Organic Synthesis Group, Institut de Chimie Moléculaire et des Matériaux d’Orsay – ICMMO (CNRS UMR 8182), Université Paris-Sud, 15 rue Georges Clémenceau, 91405 Orsay cedex, France   Fax: +39(70)6754388
,
Francesco Secci*
a   Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042 Monserrato (Cagliari), Italy   Email: fsecci@unica.it
,
Pier Paolo Piras
a   Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042 Monserrato (Cagliari), Italy   Email: fsecci@unica.it
,
Régis Guillot
b   CP3A Organic Synthesis Group, Institut de Chimie Moléculaire et des Matériaux d’Orsay – ICMMO (CNRS UMR 8182), Université Paris-Sud, 15 rue Georges Clémenceau, 91405 Orsay cedex, France   Fax: +39(70)6754388
› Author Affiliations
Further Information

Publication History

Received: 11 September 2014

Accepted after revision: 13 October 2014

Publication Date:
11 November 2014 (online)


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Abstract

A new procedure for the desymmetrization of prochiral 3-substituted cyclobutanones has been established through organocatalyzed Michael addition to nitroalkenes. The approach provides enantiomerically enriched 2-alkyl-3-aryl(alkyl) cyclobutanones with three contiguous stereogenic centers. The optimum conditions were determined by screening of catalyst and reaction conditions and a transition-state model is proposed to account for the observed diastereomeric and enantiomeric selectivities.

Supporting Information