Diastereo- and Enantioselective Syntheses of (−)-Coniine, (−)-Solenopsin A, (−)-Solenopsis fugaz venom and (−)-Xenovenine via Deoxygenative Decarboxylation of 2-Carbonylsultam-Substituted N-Hydroxy-Piperidines and -Pyrrolidines

Von Oppolzer, Wolfgang; Bochet, Christian; Merifield, Eric

doi:10.1016/0040-4039(94)88213-4

Scientific article

Letter

English

Diastereo- and Enantioselective Syntheses of (−)-Coniine, (−)-Solenopsin A, (−)-Solenopsis fugaz venom and (−)-Xenovenine via Deoxygenative Decarboxylation of 2-Carbonylsultam-Substituted N-Hydroxy-Piperidines and -Pyrrolidines

ContributorsVon Oppolzer, Wolfgang; Bochet, Christian; Merifield, Eric

Published inTetrahedron Letters, vol. 35, no. 38, p. 7015-7018

Publication date1994

Abstract

Heating cyclic 2-carbonylsultam-substituted N-hydroxylamines 4 with NaH yields sultam auxiliary 8 and imines 10, which are trapped in situ either by i-Bu2AlH or organocerium reagents to give enantiomerically pure 2-mono- or trans-2,6(2,5)-disubstituted piperidines (pyrrolidines) 11 or 12.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, BOCHET, Christian, MERIFIELD, Eric. Diastereo- and Enantioselective Syntheses of (−)-Coniine, (−)-Solenopsin A, (−)-Solenopsis fugaz venom and (−)-Xenovenine via Deoxygenative Decarboxylation of 2-Carbonylsultam-Substituted N-Hydroxy-Piperidines and -Pyrrolidines. In: Tetrahedron Letters, 1994, vol. 35, n° 38, p. 7015–7018. doi: 10.1016/0040-4039(94)88213-4

Article (Published version)

Identifiers

PID : unige:151913
DOI : 10.1016/0040-4039(94)88213-4

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/0040403994882134

Journal ISSN0040-4039

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Diastereo- and Enantioselective Syntheses of (−)-Coniine, (−)-Solenopsin A, (−)-Solenopsis fugaz venom and (−)-Xenovenine via Deoxygenative Decarboxylation of 2-Carbonylsultam-Substituted N-Hydroxy-Piperidines and -Pyrrolidines

Heating cyclic 2-carbonylsultam-substituted N-hydroxylamines 4 with NaH yields sultam auxiliary 8 and imines 10, which are trapped in situ either by i-Bu2AlH or organocerium reagents to give enantiomerically pure 2-mono- or trans-2,6(2,5)-disubstituted piperidines (pyrrolidines) 11 or 12.

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