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 journalArticle

14 Citations (Scopus)

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 languageEnglish
Pages (from-to)167-190
Number of pages24
JournalArkivoc
Volume2007
Issue number5
Publication statusPublished - 2007
Externally publishedYes

Fingerprint

Cycloaddition
Chemical activation
naphthosultone
Hot Temperature

Keywords

  • Asymmetric synthesis
  • Cycloadditions
  • Debenzylation
  • High pressure
  • Sulfur heterocycles

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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 journalArticle

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