STEREOSELECTIVE SYNTHESIS OF (2S,3S)-3-N-BENZYLAMINOPROLINOL AND (7S,8R)-7-N-BENZYLAMINOPYRROLIZIDIN-3-ONE

Authors
LANGLOIS N RADOM MO
Citation
N. Langlois et Mo. Radom, STEREOSELECTIVE SYNTHESIS OF (2S,3S)-3-N-BENZYLAMINOPROLINOL AND (7S,8R)-7-N-BENZYLAMINOPYRROLIZIDIN-3-ONE, Tetrahedron letters, 39(8), 1998, pp. 857-860
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
8
Year of publication
1998
Pages
857 - 860
Database
ISI
SICI code
0040-4039(1998)39:8<857:SSO(A(>2.0.ZU;2-X
Abstract
The highly stereoselective synthesis of of (2S,3S)-3N-benzylaminoproli nol and derivatives involved the conjugate addition of N-benzylamine t o alpha,beta-unsaturated lactam 2. Wittig-Horner reactions with 1-acet yl-3-N-acetyl-N-benzylaminoprolinal provided a simple access to (7S,8R )-7-N-benzylaminopyrrolizidin-3-one. (C) 1998 Published by Elsevier Sc ience Ltd. All rights reserved.