Organic & Biomolecular Chemistry 2006-05-21

Reactivity of cyclic sulfamidates towards sulfur-stabilised enolates. Stereocontrolled synthesis of functionalised lactams.

John F Bower, Suda Chakthong, Jakub Svenda, Andrew J Williams, Ron M Lawrence, Peter Szeto, Timothy Gallagher

Index: Org. Biomol. Chem. 4(10) , 1868-77, (2006)

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Abstract

A structurally representative series of 1,2- and 1,3-cyclic sulfamidates react with enolates derived from methyl alpha-phenylthioacetate 9b to give 5- and 6-substituted alpha-phenylthio lactams 20-24. These products provide, via the corresponding sulfoxides, an entry to alpha,beta-unsaturated lactams e.g. 12, 27, 29 and their alpha-phenylthio analogues e.g. 26 and 30. With the enantiomerically pure 1,2-cyclic sulfamidates 10, 15 and 17, these reactions all proceed with no detectable loss of stereochemical integrity.