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

被引：97
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.
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页码：9707 / 9718
页数：12
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