Enantiomerically pure isoxazolines via addition of nitrile oxides to chiral N-acryloyl toluene-2,α-sultams

Von Oppolzer, Wolfgang; Kingma, Arend Jouke; Pillai, Sasikumar Krishna

doi:10.1016/S0040-4039(00)93489-0

Scientific article

Letter

English

Enantiomerically pure isoxazolines via addition of nitrile oxides to chiral N-acryloyl toluene-2,α-sultams

ContributorsVon Oppolzer, Wolfgang; Kingma, Arend Jouke; Pillai, Sasikumar Krishna

Published inTetrahedron Letters, vol. 32, no. 37, p. 4893-4896

Publication date1991

Abstract

New saccharine-derived, crystalline acryloylsultams 12 undergo efficient 1,3-dipolar cycloadditions of nitrile oxides with ≥95:5 stereoface discrimination. Products 13 or 14 are purified by simple crystallization and cleaved with recovery of the chirophore to provide optically pure Δ²-isoxazolines 15.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, KINGMA, Arend Jouke, PILLAI, Sasikumar Krishna. Enantiomerically pure isoxazolines via addition of nitrile oxides to chiral N-acryloyl toluene-2,α-sultams. In: Tetrahedron Letters, 1991, vol. 32, n° 37, p. 4893–4896. doi: 10.1016/S0040-4039(00)93489-0

Article (Published version)

Identifiers

PID : unige:152455
DOI : 10.1016/S0040-4039(00)93489-0

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900934890

Journal ISSN0040-4039

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Enantiomerically pure isoxazolines via addition of nitrile oxides to chiral N-acryloyl toluene-2,α-sultams

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