Synthesis of aziridine-2-carboxylates via conjugate addition of an amine to 2-(5H)-furanon-3-yl methanesulfonate: application to the preparation of alpha-amino-beta-hydroxy-gamma-butyrolactone

Authors
de Saint-Fuscien, C Dodd, RH
Citation
C. De Saint-fuscien et Rh. Dodd, Synthesis of aziridine-2-carboxylates via conjugate addition of an amine to 2-(5H)-furanon-3-yl methanesulfonate: application to the preparation of alpha-amino-beta-hydroxy-gamma-butyrolactone, TETRAHEDR L, 41(17), 2000, pp. 3061-3064
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
17
Year of publication
2000
Pages
3061 - 3064
Database
ISI
SICI code
0040-4039(20000422)41:17<3061:SOAVCA>2.0.ZU;2-W
Abstract
Conjugate addition of benzylamine to 2-(5H)-furanon-3-yl methanesulfonate i n methanol afforded a 7:1 mixture of the trans and cis methyl N-benzyl-2-hy droxymethylaziridine-2-carboxylates 7 and 8, respectively. Treatment of 7 w ith benzyl alcohol in the presence of BF3. OEt2 then furnished, after hydro genolysis, rac-cis alpha-amino-beta-hydroxy-gamma-butyrolactone (1). (C) 20 00 Elsevier Science Ltd. All rights reserved.