NON-DECARBOXYLATIVE 1,3-DIPOLAR CYCLOADDITIONS OF IMINES OF ALPHA-AMINO-ACIDS AS A ROUTE TO PROLINE DERIVATIVES

Authors
ALY MF YOUNES MI METWALLY SAM
Citation
Mf. Aly et al., NON-DECARBOXYLATIVE 1,3-DIPOLAR CYCLOADDITIONS OF IMINES OF ALPHA-AMINO-ACIDS AS A ROUTE TO PROLINE DERIVATIVES, Tetrahedron, 50(10), 1994, pp. 3159-3168
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
10
Year of publication
1994
Pages
3159 - 3168
Database
ISI
SICI code
0040-4020(1994)50:10<3159:N1COIO>2.0.ZU;2-1
Abstract
alpha-Amino acids react with aryl aldehydes in the presence of N-subst ituted maleimides to yield stereospecific cycloadducts (3a,b) with dim ethyl fumarate to give isometric mixtures of (4a-i) and (5a-i). The re latively low yield in the case of dimethyl fumarate is presumably due to the steric interaction between the dipolarophile and the substituen ts at both ends of the dipole.