Asymmetric synthesis of (-)-psendoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions

Authors
Testa, ML Hajji, C Zaballos-Garcia, E Garcia-Segovia, AB Sepulveda-Arques, J
Citation
Ml. Testa et al., Asymmetric synthesis of (-)-psendoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions, TETRAHEDR-A, 12(9), 2001, pp. 1369-1372
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
9
Year of publication
2001
Pages
1369 - 1372
Database
ISI
SICI code
0957-4166(20010611)12:9<1369:ASO(F(>2.0.ZU;2-C
Abstract
A ring-opening reaction of N-methylaziridines with Boc(2)O/NaI has been app lied to the asymmetric synthesis of pseudoephedrine. 3-Methylamino-3-phenyl -1,2-propanediol 1, derived from (2S,3S)-3-phenyloxiran-2-ylmethanol, was c onverted into the oxazolidin-2-one 4, a precursor of pseudoephedrine. The r eaction occurs with a stereospecific interchange of amino and alcohol funct ions. (C) 2001 Elsevier Science Ltd. All rights reserved.