SYNTHESIS OF OPTICALLY-ACTIVE ARYLENE BIS-ALANINE DERIVATIVES CARRYING ORTHOGONAL PROTECTING GROUPS

Authors
RITZEN A BASU B CHATTOPADHYAY SK DOSSA F FREJD T
Citation
A. Ritzen et al., SYNTHESIS OF OPTICALLY-ACTIVE ARYLENE BIS-ALANINE DERIVATIVES CARRYING ORTHOGONAL PROTECTING GROUPS, Tetrahedron : asymmetry, 9(3), 1998, pp. 503-512
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
3
Year of publication
1998
Pages
503 - 512
Database
ISI
SICI code
0957-4166(1998)9:3<503:SOOABD>2.0.ZU;2-U
Abstract
Derivatives of para- and meta-phenylene bis-alanine and related biphen yl systems, carrying four orthogonal protecting groups, were synthesis ed via combinations of Heck couplings and asymmetric hydrogenations, T he intermediate unsaturated arylalanine derivatives were hydrogenated using [Rh(COD)((R,R)-DIPAMP)]+BF4- or [Rh(COD)(Me-DuPHOS)]X-+(-) as ca talysts to produce the optically active, protected amino acid derivati ves in greater than or equal to 98% e.e. as analysed by chiral phase H PLC. (C) 1998 Elsevier Science Ltd. All rights reserved.