Tetrahedron

Amidoalkylation of aromatics with glyoxylic acid-γ-lactam adducts: 2-pyrrolidinone, pyroglutamic acid amide and ester

E Roth, J Altman, M Kapon, D Ben-Ishai

Index: Roth, Ecaterina; Altman, Janina; Kapon, Moshe; Ben-Ishai, Dov Tetrahedron, 1995 , vol. 51, # 3 p. 801 - 810

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Citation Number: 19

Abstract

A glyoxylic acid-2-pyrrolidinone adduct leads to N-acyliminium-ion induced intermolecular electrophilic aromatic substitution yielding nitrogen-substituted phenylglycine derivatives, whereas the benzylamide of glyoxylic acid-2-pyrrolidinone adduct undergoes intramolecular amidoalkylation to give an isoquinolone type compound. High stereospecifity and enantioselectivity was observed in intermolecular amidoalkylation of benzene using ...

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