AMIDOALKYLATION OF AROMATICS WITH GLYOXYLIC ACID-GAMMA-LACTAM ADDUCTS- 2-PYRROLIDINONE, PYROGLUTAMIC ACID AMIDE AND ESTER

Authors
ROTH E ALTMAN J KAPON M BENISHAI D
Citation
E. Roth et al., AMIDOALKYLATION OF AROMATICS WITH GLYOXYLIC ACID-GAMMA-LACTAM ADDUCTS- 2-PYRROLIDINONE, PYROGLUTAMIC ACID AMIDE AND ESTER, Tetrahedron, 51(3), 1995, pp. 801-810
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
3
Year of publication
1995
Pages
801 - 810
Database
ISI
SICI code
0040-4020(1995)51:3<801:AOAWGA>2.0.ZU;2-P
Abstract
A glyoxylic acid-2-pyrrolidinone adduct leads to N-acyliminium-ion ind uced intermolecular electrophilic aromatic substitution yielding nitro gen-substituted phenylglycine derivatives, whereas the benzylamide of glyoxylic acid-2-pyrrolidinone adduct undergoes intramolecular amidoal kylation to give an isoquinolone type compound. High stereospecifity a nd enantioselectivity was observed in intermolecular amidoalkylation o f benzene using glyoxylic acid-S-pyroglutamic acid ester or amide addu cts.