Synthesis 2008(3): 485-489  
DOI: 10.1055/s-2007-990864
PSP
© Georg Thieme Verlag Stuttgart · New York

The Reaction of Nitrones with Cyclopropanes: A Convenient Preparation of Tetrahydro-1,2-oxazines

Cheryl A. Carson, Ian S. Young, Michael A. Kerr*
Department of Chemistry, The University of Western Ontario, London, ON, N6A 5B7, Canada
Fax: +1(519)6613022; e-Mail: [email protected];
Further Information

Publication History

Received 17 July 2007
Publication Date:
29 October 2007 (online)

Abstract

Nitrones and dialkyl cyclopropane-1,1-dicarboxylates undergo smooth reaction in the presence of ytterbium(III) triflate to form tetrahydro-1,2-oxazines with a high degree of regio- and stereocontrol. A three-component protocol has also been developed wherein the nitrone is generated in situ from an aldehyde and a hydroxylamine. The reactions are often high yielding with broad substrate scope. The multicomponent nature of the reaction makes it amenable to the synthesis of compound libraries and also allows for highly convergent strategies to be developed in target-oriented synthesis.

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