Studies Dealing with Thionium Ion Promoted Mannich Cyclization Reactions

A Padwa, AG Waterson

Index: Padwa, Albert; Waterson, Alex G. Journal of Organic Chemistry, 2000 , vol. 65, # 1 p. 235 - 244

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Citation Number: 60

Abstract

Treatment of several amido-substituted thioacetals with dimethyl (methylthio) sulfonium tetrafluoroborate (DMTSF) produces synthetically useful thionium ions that are intercepted by the adjacent nitrogen atom to afford both five-and six-membered alkylthio-substituted lactams as transient intermediates. Further reaction of the alkylthio-substituted lactam with DMTSF generates an N-acyliminium ion, which undergoes cyclization with the tethered ...