Steric reversal of the endo-selectivity effect in 1,8-dipolar cycloadditions of phthalazinium-2-ylides with N-substituted maleimides: Endo- and exo-1,2(dicarboxy-N-substituted imido)-1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazines

被引:3
作者
Butler, RN [1 ]
Farrell, DM [1 ]
机构
[1] Univ Coll Galway, Dept Chem, Galway, Ireland
来源
JOURNAL OF CHEMICAL RESEARCH-S | 1998年 / 04期
关键词
D O I
10.1039/a708237a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-Methyl- and N-aryl-maleimides undergo cycloadditions with phthalazinium-2-dicyanomethanide and -2-unsubstituted methanide 1,3-dipoles to give exclusive or predominant endo-cycloadducts but with N-tert-butylmaleimide this endo effect is reversed to favour the exo-cycloadducts exo-1,2-(dicarboxy-N-tert-butylimido)-1,2,3,10b-tetrahydropyrrolo[2,1-a]phthalazines 11 and 15.
引用
收藏
页码:214 / 215
页数:3
相关论文
共 14 条
[1]   DIELS-ALDER REACTION OF UNSYMMETRICAL DIENES WITH METHYL ACRYLATE [J].
ANSELL, MF ;
CLEMENTS, AH .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (02) :275-&
[2]  
Butler RN, 1996, J CHEM RES-S, P418
[3]   REMOVAL OF SULFUR GROUPS FROM MOLECULES BY COPPER(I) - PREPARATION OF SULFUR-SUBSTITUTED 1,3-DIENES FOR DIELS-ALDER REACTION [J].
COHEN, T ;
MURA, AJ ;
SHULL, DW ;
FOGEL, ER ;
RUFFNER, RJ ;
FALCK, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (19) :3218-3219
[4]  
COOKSON RC, 1966, J CHEM SOC CHEM COMM, P15
[5]   VARIATIONS IN THE STEREOCHEMISTRY OF THE BORON-TRIFLUORIDE MEDIATED CYCLOCONDENSATION REACTION OF ALDEHYDES WITH SILOXY DIENES [J].
DANISHEFSKY, S ;
CHAO, KH ;
SCHULTE, G .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4650-4652
[6]   ON THE SCOPE, MECHANISM, AND STEREOCHEMISTRY OF THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF ACTIVATED DIENES WITH ALDEHYDES - AN APPLICATION TO THE ERYTHRONOLIDE PROBLEM [J].
DANISHEFSKY, SJ ;
LARSON, E ;
ASKIN, D ;
KATO, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1246-1255
[7]  
GHASEZ L, 1994, STEREOCONTROLLED ORG, P200
[8]  
GUNNER O, 1988, J ORG CHEM, V53, P5348
[9]  
KOBUKE Y, 1970, J AM CHEM SOC, V92, P6548
[10]  
KOBUKE Y, 1972, J AM CHEM SOC, V94, P1587