Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides

Abstract

A range of novel γ- and δ-sultams was prepared by intramolecular [4+2] cycloaddition of vinylsulfonamides with purely thermal activation and under high pressure. Using N-1-phenylethyl substituted vinylsulfonamides, enantiopure sultams were readily obtained, debenzylation of which provided the corresponding NH sultams in high yields in the case of δ-sultams.

Original language	English
Pages (from-to)	167-190
Number of pages	24
Journal	Arkivoc
Volume	2007
Issue number	5
Publication status	Published - 2007
Externally published	Yes

Keywords

Asymmetric synthesis
Cycloadditions
Debenzylation
High pressure
Sulfur heterocycles

ASJC Scopus subject areas

Organic Chemistry

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title = "Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides",

abstract = "A range of novel γ- and δ-sultams was prepared by intramolecular [4+2] cycloaddition of vinylsulfonamides with purely thermal activation and under high pressure. Using N-1-phenylethyl substituted vinylsulfonamides, enantiopure sultams were readily obtained, debenzylation of which provided the corresponding NH sultams in high yields in the case of δ-sultams.",

keywords = "Asymmetric synthesis, Cycloadditions, Debenzylation, High pressure, Sulfur heterocycles",

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

year = "2007",

language = "English",

volume = "2007",

pages = "167--190",

journal = "Arkivoc",

issn = "1424-6376",

publisher = "Arkat USA",

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T1 - Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides

AU - Rogachev, Victor O.

AU - Metz, Peter

PY - 2007

Y1 - 2007

N2 - A range of novel γ- and δ-sultams was prepared by intramolecular [4+2] cycloaddition of vinylsulfonamides with purely thermal activation and under high pressure. Using N-1-phenylethyl substituted vinylsulfonamides, enantiopure sultams were readily obtained, debenzylation of which provided the corresponding NH sultams in high yields in the case of δ-sultams.

AB - A range of novel γ- and δ-sultams was prepared by intramolecular [4+2] cycloaddition of vinylsulfonamides with purely thermal activation and under high pressure. Using N-1-phenylethyl substituted vinylsulfonamides, enantiopure sultams were readily obtained, debenzylation of which provided the corresponding NH sultams in high yields in the case of δ-sultams.

KW - Asymmetric synthesis

KW - Cycloadditions

KW - Debenzylation

KW - High pressure

KW - Sulfur heterocycles

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