ELECTROGENERATED CHIRAL CATIONIC GLYCINE EQUIVALENTS - PART-1 - THE 6-METHOXY DERIVATIVE OF CYCLO(L-PRO-GLY)

Authors
KARDASSIS G BRUNGS P STECKHAN E
Citation
G. Kardassis et al., ELECTROGENERATED CHIRAL CATIONIC GLYCINE EQUIVALENTS - PART-1 - THE 6-METHOXY DERIVATIVE OF CYCLO(L-PRO-GLY), Tetrahedron, 54(14), 1998, pp. 3471-3478
Citations number
41
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
14
Year of publication
1998
Pages
3471 - 3478
Database
ISI
SICI code
0040-4020(1998)54:14<3471:ECCGE->2.0.ZU;2-E
Abstract
The cyclic N,O-acetal cyclo(L-Pro-Gly(OMe)OMe (8) has proved to be an effective chiral electrophilic glycine equivalent which is applicable in nucleophilic substitution reactions not only under Broenstedt acid catalysis but also under Lewis acid catalysis with excellent diastereo selectivities. This chiral building block can easily be obtained by el ectrochemical methoxylative decarboxylation of the cyclic dipeptide 6 generated from L-proline and aminomalonic diester. Thus, enantiomerica lly pure D-allyl glycine has been generated. (C) 1998 Elsevier Science Ltd. All rights reserved.