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A mild and efficient method for the preparation of n-tosyl amides and lactams

✍ Scribed by David Tanner; Peter Somfai

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 277 KB
Volume: 44
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85848-8

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✦ Synopsis

N-tosyl amides and lactams can be prepared easily and under mild conditions by the inter-or intramolecular condensation of carboxylic acids and secondary sulfonamides. The coupling reagent used is dicyclohaxylcarbodiimide (DCC) in the presence of 4-pyrrolidioopyridine (4-PPY) and the reactions proceed readily, usually in high yield, at room temperature.

serendipitous discovery that the g-sulfonamide carboxylic acid shown in Eq. 1 could be cyclised rapidly (15 min. at RT) to the corresponding N-tosyl g-lactam in axcellent yield. This reaction was one of the key steps in the enantioselective route to the carbapanem antibiotic (+)-PS-5 which is described ih the following paper', while the present report deals with the scope and limitations of the inter-and intramolecular varieties 0. 4 this novel coupling reaction (Eq. 2 and 2).

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