DIASTEREOSELECTIVE DIELS-ALDER REACTIONS BETWEEN SUBSTITUTED 1,3-BUTADIENES AND N-ALPHA-METHYLBENZYLMALEIMIDE

被引:34
作者
BALDWIN, SW
GREENSPAN, P
ALAIMO, C
MCPHAIL, AT
机构
[1] Department of Chemistry Duke University Durham
关键词
D O I
10.1016/S0040-4039(00)79415-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The TiCl4 catalyzed reaction between 2-t-butyl-1,3-butadiene and N-alpha-methylbenzylmaleimide at -65-degrees-C affords diastereomeric Diels-Alder adducts in a 15:1 ratio. The structure of the major adduct was determined by x-ray.
引用
收藏
页码:5877 / 5880
页数:4
相关论文
共 18 条
[1]  
Backer HJ, 1943, RECL TRAV CHIM PAY-B, V62, P561
[2]  
Backer HJ, 1934, RECL TRAV CHIM PAY-B, V53, P525
[3]  
CARRUTHERS W, 1990, CYCLOADDITION REACTI, P61
[4]   RATE OF REACTION OF MALEIC ANHYDRIDE WITH 1,3-DIENES AS RELATED TO DIENE CONFORMATION [J].
CRAIG, D ;
FOWLER, RB ;
SHIPMAN, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (13) :2885-&
[5]  
DOIUCHI T, 1984, EUR POLYM J, V20, P831, DOI 10.1016/0014-3057(84)90121-6
[6]   ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].
EVANS, DA ;
CHAPMAN, KT ;
BISAHA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256
[7]   LEWIS ACID CATALYSIS OF DIELS-ALDER REACTIONS [J].
HOUK, KN ;
STROZIER, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (12) :4094-4096
[8]  
KERGOMARD A, 1975, B SOC CHIM FR II-CH, P297
[9]  
KWART H, 1972, J AM CHEM SOC, V74, P3094
[10]  
MARVEL CS, 1968, J ORG CHEM, V23, P1658