Catalytic asymmetric hydrogenation of beta-substituted alpha,beta,gamma,delta-unsaturated amino acids

Authors
Burk, MJ Bedingfield, KM Kiesman, WF Allen, JG
Citation
Mj. Burk et al., Catalytic asymmetric hydrogenation of beta-substituted alpha,beta,gamma,delta-unsaturated amino acids, TETRAHEDR L, 40(16), 1999, pp. 3093-3096
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
16
Year of publication
1999
Pages
3093 - 3096
Database
ISI
SICI code
0040-4039(19990416)40:16<3093:CAHOBA>2.0.ZU;2-P
Abstract
The Rh-DuPHOS and Rh-BPE catalyzed hydrogenation of beta-substituted alpha, beta,gamma,delta-unsaturated amino acids establishes two contiguous stereog enic centers simultaneously. Both high regioselectivity and good to excelle nt enantioselectivity have been demonstrated in this process leading to bet a-branched allyl glycine derivatives. Enamide geometry was found to influen ce stereoselectivity. Studies aimed at defining the scope and limitations o f this process are described. (C) 1999 Elsevier Science Ltd. All rights res erved.