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

被引：19

作者：

ROTH, E

ALTMAN, J

KAPON, M

BENISHAI, D

机构：

[1] Department of Chemistry, Technion - Israel Institute of Technology, Technion City, Haifa

来源：

TETRAHEDRON | 1995年 / 51卷 / 03期

关键词：

D O I：

10.1016/0040-4020(94)00952-Q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 glyoxylic acid-S-pyroglutamic acid ester or amide adducts.

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页码：801 / 810

页数：10

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