Base-catalyzed cyclization of N-sulfonyl propargylamides to sulfonylmethyl-substituted oxazoles via sulfonyl migration.

TitleBase-catalyzed cyclization of N-sulfonyl propargylamides to sulfonylmethyl-substituted oxazoles via sulfonyl migration.
Publication TypeJournal Article
Year of Publication2013
AuthorsYu X, Xin X, Wan B, Li X
JournalThe Journal of organic chemistry
Volume78
Issue10
Pagination4895-904
Date Published2013 May 17
Abstract

The reaction of N-sulfonyl propargylamides in the presence of a base catalyst selectively affords 5-sulfonylmethyl oxazoles via 1,4-sulfonyl migration. Allenes have been established as the key intermediates. Experimental evidence has been provided to support a two-step mechanism in the cyclization.

DOI10.1111/tpj.12228
Alternate JournalJ. Org. Chem.