DIASTEREOSELECTIVE AZA-DIELS-ALDER REACTION - USE OF 1-PHENYLETHYLIMINE OF ALKYL GLYOXYLATE FOR SYNTHESIS OF CYCLIC ALPHA-AMINO-ACIDS

被引：98

作者：

ABRAHAM, H ^{[1
]}

STELLA, L ^{[1
]}

机构：

[1] UNIV MARSEILLE 3,FAC SCI ST JEROME,CNRS,CHIM ORGAN LAB B,AVE NORMANDIE NIEMEN,F-13397 MARSEILLE 13,FRANCE

来源：

TETRAHEDRON | 1992年 / 48卷 / 44期

关键词：

DIASTEREOSELECTIVE SYNTHESIS; AZA-DIELS-ALDER REACTIONS; ALPHA-AMINO-ACIDS;

D O I：

10.1016/S0040-4020(01)81187-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of trifluoroacetic acid-boron trifluoride combination is highly effective in dichloromethane for the activation of 1-phenylethylimine of methyl or ethyl glyoxylates as heterodienophiles in Diels-Alder cycloaddition reactions with a series of conjugated dienes. High regio-(meta:para) and stereo-(endo:exo) selectivities are observed at low temperature. Asymmetric induction is very high (>98%) with cyclopentadiene but remains low in the other cases.

引用

页码：9707 / 9718

页数：12

共 53 条

[1] HETEROCYCLEN DURCH DIENSYNTHESE .2. N-[BUTYLOXYCARBONYLMENTHYLEN]-P-TOLUOLSULFONAMID EIN NEUES DIENOPHIL ZUR DARSTELLUNG VON PYRIDIN- PIPERIDEIN- UND PIPERIDIN-DERIVATEN DURCH DIELS-ALDER-SYNTHESE [J].