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

Victor O. Rogachev, Peter Metz

Research output: Contribution to journal › Article

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

Fingerprint

Cycloaddition

Chemical activation

naphthosultone

Hot Temperature

Keywords

Asymmetric synthesis
Cycloadditions
Debenzylation
High pressure
Sulfur heterocycles

ASJC Scopus subject areas

Organic Chemistry

Cite this

Rogachev, V. O., & Metz, P. (2007). Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides. Arkivoc, 2007(5), 167-190.

Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides. / Rogachev, Victor O.; Metz, Peter.

In: Arkivoc, Vol. 2007, No. 5, 2007, p. 167-190.

Research output: Contribution to journal › Article

Rogachev, VO & Metz, P 2007, 'Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides', Arkivoc, vol. 2007, no. 5, pp. 167-190.

Rogachev VO, Metz P. Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides. Arkivoc. 2007;2007(5):167-190.

Rogachev, Victor O. ; Metz, Peter. / Stereoselective preparation of γ- and δ-sultams by thermal and high-pressure intramolecular Diels-Alder reaction of vinylsulfonamides. In: Arkivoc. 2007 ; Vol. 2007, No. 5. pp. 167-190.

@article{d4c92bc724fc4d88ab4007f7ce1c3aff,

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",

number = "5",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=33846243270&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33846243270&partnerID=8YFLogxK

M3 - Article

VL - 2007

SP - 167

EP - 190

JO - Arkivoc

JF - Arkivoc

SN - 1424-6376

IS - 5