Regiospecific and enantiospecific ring opening of methyl (+)-(1 ' R,2R)- and (-)-(1 ' R,2S)-1-(2-phenylethanol) aziridine-2-carboxylates

Authors
Gnecco, D Orea, L Galindo, A Enriquez, RG Toscano, RA Reynolds, WF
Citation
D. Gnecco et al., Regiospecific and enantiospecific ring opening of methyl (+)-(1 ' R,2R)- and (-)-(1 ' R,2S)-1-(2-phenylethanol) aziridine-2-carboxylates, MOLECULES, 5(8), 2000, pp. 998-1003
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
MOLECULES
ISSN journal
14203049 → ACNP
Volume
5
Issue
8
Year of publication
2000
Pages
998 - 1003
Database
ISI
SICI code
1420-3049(2000)5:8<998:RAEROO>2.0.ZU;2-5
Abstract
The acid-catalyzed ring-opening of methyl (+)-(1'R, 2R) and (-)-(1'R, 2S)-1 -(2-phenylethanol) aziridine-2-carboxylates (1) and (2) lead quantitatively to the corresponding 2(S)-(-)-chloro-3-[2'-hydroxy-1'(R)-phenyl-ethylamino ] propionic acid methyl ester (3) and 2(R)-(-)-chloro-3-[2'-hydroxy-1'(R)-p henyl-ethylamino] propionic acid methyl ester (4) hydrochlorides.