Synlett 2011(1): 89-93  
DOI: 10.1055/s-0030-1259084
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Unexpected Formation of Optically Active 4-Substituted 5-Hydroxy-γ-
lactams by Organocatalyzed Reaction of 3-Substituted Cyclobutanones with Nitrosobenzene

Francesca Capittaa,b, Angelo Frongia*a, Jean Ollivierb, Pier Paolo Piras*a, Francesco Seccia
a Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042 Monserrato (Cagliari), Italy
Fax: +39(070)6754388; e-Mail: angelo.frongia@gmail.com; e-Mail: pppiras@unica.it;
b UMR 8182, Laboratoire de Synthèse Organique et Méthodologie, ICMMO, Université Paris-Sud 11, 91405 Orsay Cedex, France
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Publikationsverlauf

Received 7 September 2010
Publikationsdatum:
07. Dezember 2010 (online)

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Abstract

An organocatalyzed enantioselective desymmetrization reaction for converting 3-substituted cyclobutanones into 4-substituted 5-hydroxy-γ-lactams is presented. This involves a ring-expanding O-nitroso aldol-cyclization domino sequence. This synthetic protocol provides access to five-membered ring systems in good yields with the generation of two new stereogenic centers.