Asymmetric synthesis of 4-substituted prolines as conformationally constrained amino acid analogues

Authors
Wang, Q Sasaki, NA Potier, P
Citation
Q. Wang et al., Asymmetric synthesis of 4-substituted prolines as conformationally constrained amino acid analogues, TETRAHEDRON, 54(52), 1998, pp. 15759-15780
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
54
Issue
52
Year of publication
1998
Pages
15759 - 15780
Database
ISI
SICI code
0040-4020(199812)54:52<15759:ASO4PA>2.0.ZU;2-P
Abstract
Treatment of readily available chiral building block 1 with (2R)-2,3-O-isop ropylideneglyceraldehyde (5) provides a new route for asymmetric synthesis of 2,4-disubstituted pyrrolidines. Several proline-amino acid chimeras: pro line-leucine, proline-lysine, proline-arginine and proline-glutamic acid, a re synthesized in highly diastereomerically pure forms, (C) 1998 Elsevier S cience Ltd. All rights reserved.