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Synfacts 2008(4): 0348-0348  
DOI: 10.1055/s-2008-1042851
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

A Lateral Metallation Strategy for 1,2-Benzothiazin-3-one 1,1-Dioxides

Contributor(s): Victor Snieckus, Johnathan Board
A. O. Aliyenne, J. Kraïem, Y. Kacem, B. B. Hassine*
Faculté des Sciences de Monastir, Tunisia
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

Reported is the formation of enantio­merically pure 1,2-benzothiazin-3-one 1,1-dioxide derivatives using a sequence of lateral metallation, cyclization and ring-opening of 3-N-mesitylenesulfonyl-1,3-oxazolidin-2-ones. Starting materials are readily available from amino ­acids. A plausible mechanism invoking a complex-induced proximity effect (CIPE) leading to the formation of an ortho-tolyl lithiated species coordinated with the oxazolidinone ring is proposed.