CYCLOADDITION REACTIONS OF GAMMA-AMINO ALPHA,BETA-DIDEHYDRO AMINO-ACID ESTERS - A TEST CASE FOR THE PRINCIPLE OF 1,3-ALLYLIC STRAIN

被引：41
|
作者：
REETZ, MT [1 ]
KAYSER, F [1 ]
HARMS, K [1 ]
机构：
[1] UNIV MARBURG,FACHBEREICH CHEM,W-3550 MARBURG,GERMANY
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 24期
关键词：
D O I：
10.1016/S0040-4039(00)92661-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N,N-Dibenzylainino aldehydes, readily accessible from amino acids, can be converted into gamma-N,N-dibenzylamino alpha,beta-didehydro amino acid esters without racemization; these undergo stereoselective Diels-Alder reactions and 1,3-dipolar cycloaddition with diazomethane, the sense of diastereoselectivity being opposite to that predicted by the conventional principle of 1,3-allylic strain.
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页码：3453 / 3456
页数：4
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