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Synthesis 2011(13): 2165-2174  
DOI: 10.1055/s-0030-1260606
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

RuO4-Catalyzed Oxidation Reactions of N-Alkylisoxazolino-2-azanorbornane Derivatives: An Expeditious Route to Tricyclic γ-Lactams

Misal Giuseppe Memeo, Daniele (Pane) Mantione, Bruna Bovio, Paolo Quadrelli*
Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy
e-Mail: paolo.quadrelli@unipr.it;
Further Information

Publication History

Received 23 March 2011
Publication Date:
26 May 2011 (online)

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Abstract

A rapid access to conformationally constrained γ-lactams has been developed through the efficient RuO4-mediated oxidation of regioisomeric N-alkylisoxazolino-2-azanorbornane derivatives. The competition between exocyclic and endocyclic oxidation on 2-azanorbornane moieties can be driven by the proper choice of alkyl substituent on the heterocyclic nitrogen atom. Valuable bridged γ-lactams - potential analogues of classical β-lactam antibiotics - are obtained by this method.

Key Words

ruthenium tetraoxide - lactams - 1,3-dipolar cycloadditions - azanorbornenes

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22

CCDC-818258 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; E-mail: .

24

Isopropylamine hydrochloride was prepared through bubbling gaseous HCl into a cool Et2O solution of isopropylamine. The solid hydrochloride separated from the cooled solution and was collected by filtration under reduced pressure. The dried salt was used for the synthesis of the N-isopropyl-2-azanorborn-5-ene (1C).