Enantioselective preparation and hydroboration of cyclic enamides: Synthesis of (2S)-pseudoconhydrine

Von Oppolzer, Wolfgang; Bochet, Christian

doi:10.1016/0040-4039(95)00439-j

Scientific article

English

Enantioselective preparation and hydroboration of cyclic enamides: Synthesis of (2S)-pseudoconhydrine

ContributorsVon Oppolzer, Wolfgang; Bochet, Christian

Published inTetrahedron letters, vol. 36, no. 17, p. 2959-2962

Publication date1995-04-24

First online date2000-06-14

Abstract

Successive treatment of 2-alkyl-1-hydroxy-6-carbonylsultampiperidines 1 with NaH and an acylating agent/pyridine in boiling toluene affords optically pure 1-acyl-2-alkyl-1,2,3,4-tetrahydropyridines 2. Hydroboration/oxidation of N-benzoylenamides 2f and 2g furnishes trans-2-alkyl-1-benzyl-5-hydroxypiperidines5f and 5g, respectively. Hydrogenolysis of 5f provides pure (2S)-pseudoconhydrine (7), in 3 steps from 1, R2=n-C3H7 (31 % overall yield).

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, BOCHET, Christian. Enantioselective preparation and hydroboration of cyclic enamides: Synthesis of (2S)-pseudoconhydrine. In: Tetrahedron letters, 1995, vol. 36, n° 17, p. 2959–2962. doi: 10.1016/0040-4039(95)00439-j

Article (Published version)

Identifiers

PID : unige:155667
DOI : 10.1016/0040-4039(95)00439-j

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/004040399500439J

Journal ISSN0040-4039

170views

0downloads

Creation13/10/2021 12:21:00

First validation13/10/2021 12:21:00

Update16/03/2023 01:35:39

Status update16/03/2023 01:35:39

Last indexation10/06/2025 21:43:41

Archive ouverte UNIGE

Enantioselective preparation and hydroboration of cyclic enamides: Synthesis of (2S)-pseudoconhydrine

Technical informations