A HIGHLY EFFICIENT ASYMMETRIC-SYNTHESIS OF METHOXYHOMOPHENYLALANINE USING MICHAEL ADDITION OF PHENETHYLAMINE

Authors
YAMADA M NAGASHIMA N HASEGAWA J TAKAHASHI S
Citation
M. Yamada et al., A HIGHLY EFFICIENT ASYMMETRIC-SYNTHESIS OF METHOXYHOMOPHENYLALANINE USING MICHAEL ADDITION OF PHENETHYLAMINE, Tetrahedron letters, 39(49), 1998, pp. 9019-9022
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
49
Year of publication
1998
Pages
9019 - 9022
Database
ISI
SICI code
0040-4039(1998)39:49<9019:AHEAOM>2.0.ZU;2-I
Abstract
A practical method for (S)-p-methoxyhomophenylalanine (S)-1 by using d iastereoselective Michael addition as a key step was reported. Thus, t he Michael addition of(S)1-phenethylamine (S)-3 to p-methoxy-trans-ben zoylacrylic acid 2 was performed in a highly stereoselective (up to 98 % d.e. and up to 90% yield) fashion and, subsequently, the resultant a dduct 4a was catalytically hydrogenated to afford (S)-1 almost quantit atively. The most likely mechanism of the addition reaction was dynami c resolution. (C) 1998 Elsevier Science Ltd. All rights reserved.