Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides

Abstract

Vinylsulfonamides with a furan, carbocyclic, semicyclic or acyclic 1,3-diene moiety are synthetized via a domino elimination-amidation reaction of 2-chloroethanesulfonyl chloride. Intramolecular Diels-Alder reaction of these vinylsulfonamides with thermal (toluene, 110 °C) or high pressure (dichloromethane, 13 kbar) activation provides efficient access to a range of γ- and δ-sultams following a 2-3 d long synthetic procedure. Enantiopure sultams are readily obtained from N-1-phenylethyl substituted vinylsulfonamides.

Original language	English
Pages (from-to)	3076-3087
Number of pages	12
Journal	Nature Protocols
Volume	1
Issue number	6
DOIs	https://doi.org/10.1038/nprot.2006.463
Publication status	Published - 1 Jan 2007

ASJC Scopus subject areas

Biochemistry, Genetics and Molecular Biology(all)

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10.1038/nprot.2006.463

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title = "Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides",

abstract = "Vinylsulfonamides with a furan, carbocyclic, semicyclic or acyclic 1,3-diene moiety are synthetized via a domino elimination-amidation reaction of 2-chloroethanesulfonyl chloride. Intramolecular Diels-Alder reaction of these vinylsulfonamides with thermal (toluene, 110 °C) or high pressure (dichloromethane, 13 kbar) activation provides efficient access to a range of γ- and δ-sultams following a 2-3 d long synthetic procedure. Enantiopure sultams are readily obtained from N-1-phenylethyl substituted vinylsulfonamides.",

author = "Rogachev, {Victor O.} and Peter Metz",

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AB - Vinylsulfonamides with a furan, carbocyclic, semicyclic or acyclic 1,3-diene moiety are synthetized via a domino elimination-amidation reaction of 2-chloroethanesulfonyl chloride. Intramolecular Diels-Alder reaction of these vinylsulfonamides with thermal (toluene, 110 °C) or high pressure (dichloromethane, 13 kbar) activation provides efficient access to a range of γ- and δ-sultams following a 2-3 d long synthetic procedure. Enantiopure sultams are readily obtained from N-1-phenylethyl substituted vinylsulfonamides.

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Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides

Abstract

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