A CONVENIENT SYNTHESIS OF PROTECTED (R)-ALPHA-PHENYLPROLINE DERIVATIVES USING THE MITSUNOBU-REACTION

Authors
VANBETSBRUGGE J TOURWE D KAPTEIN B KIERKELS H BROXTERMAN R
Citation
J. Vanbetsbrugge et al., A CONVENIENT SYNTHESIS OF PROTECTED (R)-ALPHA-PHENYLPROLINE DERIVATIVES USING THE MITSUNOBU-REACTION, Tetrahedron, 53(27), 1997, pp. 9233-9240
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
27
Year of publication
1997
Pages
9233 - 9240
Database
ISI
SICI code
0040-4020(1997)53:27<9233:ACSOP(>2.0.ZU;2-T
Abstract
Boc-(R)-alpha-phenylproline ethyl ester 1 was prepared in good yield s tarring from racemic phenylglycine. Condensation of phenylglycine ethy l eater with benzaldehyde furnished N-benzylidene phenylglycine ethyl ester which was allylated under phase transfer catalysis conditions. A fter acidic hydrolysis, the resulting alpha-allylphenylglycine ethyl e ster was enzymatically resolved using PLE. Hydroboration and oxidation of the double bond, Boc-protection and subsequent ring closure using the Mitsunobu reaction protocol gave rise to Boc-(R)-alpha-phenylproli ne ethyl ester. (C) 1997 Elsevier Science Ltd.