NOVEL ENANTIOSELECTIVE SYNTHESIS OF TRANS-ALPHA-(2-CARBOXYCYCLOPROP-1-YL)GLYCINES - CONFORMATIONALLY CONSTRAINED L-GLUTAMATE ANALOGS

Authors
DEMIR AS TANYELI C CAGIR A TAHIR MN ULKU D
Citation
As. Demir et al., NOVEL ENANTIOSELECTIVE SYNTHESIS OF TRANS-ALPHA-(2-CARBOXYCYCLOPROP-1-YL)GLYCINES - CONFORMATIONALLY CONSTRAINED L-GLUTAMATE ANALOGS, Tetrahedron : asymmetry, 9(6), 1998, pp. 1035-1042
Citations number
43
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
6
Year of publication
1998
Pages
1035 - 1042
Database
ISI
SICI code
0957-4166(1998)9:6<1035:NESOT>2.0.ZU;2-E
Abstract
D- and L-alpha-(2-carboxycycloprop-1-yl)glycines were synthesized from trans-1,3-di(2-furyl)propenane. Conversion of the double bond to a cy clopropane is followed by-the formation of an oxime ether. Enantiosele ctive reduction of the oxime ether, separation of diastereomers and ox idation of the furane rings gave enantiomerically pure D- and L-CCG I and CCG II. The structure of oxime 7b was determined by X-ray crystal structure analysis. The key step is the oxazaborolidine catalyzed enan tioselective conversion of oxime ethers to amines. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.