Synthesis 2008(4): 594-604  
DOI: 10.1055/s-2008-1032146
PAPER
© Georg Thieme Verlag Stuttgart · New York

Benzothiazines in Synthesis: A Route to Chiral Cyclobutanes

Michael Harmata*, Weijiang Ying, Xuechuan Hong, Charles L. Barnes
Department of Chemistry, University of Missouri-Columbia, Columbia, MO 65211, USA
Fax: +1(573)8822754; e-Mail: HarmataM@missouri.edu;
Further Information

Publication History

Received 27 August 2007
Publication Date:
31 January 2008 (online)

Abstract

Using enantiomerically pure benzothiazines as templates, enantiomerically pure cyclobutanes were prepared. Such compounds are potentially interesting synthetic intermediates. The sequence developed for the preparation of these compounds, as well as some of their chemistry, is described.

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Crystallographic data (excluding structure factors) for some structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 658446 (5e), 658447 (5g), 672249 (6a), 658448 (6c), 658567 (6e), 658449 (7), and 658450 (sulfone of 7). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].