Recognition-induced control and acceleration of a pyrrole Diels-Alder reaction

被引:19
作者
Bennes, R
Babiloni, MS
Hayes, W
Philp, D
机构
[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
[2] Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(01)00149-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The formation of two hydrogen bonds between an amidopyridine and a carboxylic acid controls the stereochemical outcome and significantly accelerates the rate of the Diels-Alder cycloaddition between a benzoylpyrrole and a maleimide. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:2377 / 2380
页数:4
相关论文
共 14 条
[1]   SYNTHESIS OF ENDO-2-PHENYL-7-AZABICYCLO[2.2.1]HEPTANE VIA HIGH-PRESSURE DIELS-ALDER REACTIONS OF PYRROLES [J].
ABEN, RWM ;
KEIJSERS, J ;
HAMS, B ;
KRUSE, CG ;
SCHEEREN, HW .
TETRAHEDRON LETTERS, 1994, 35 (08) :1299-1300
[2]   DIELS-ALDER REACTIONS CATALYZED BY CATION-EXCHANGED CLAY-MINERALS [J].
ADAMS, JM ;
DYER, S ;
MARTIN, K ;
MATEAR, WA ;
MCCABE, RW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06) :761-765
[3]   Recognition-mediated facilitation of a disfavored Diels-Alder reaction [J].
Bennes, R ;
Philp, D ;
Spencer, N ;
Kariuki, BM ;
Harris, KDM .
ORGANIC LETTERS, 1999, 1 (07) :1087-1090
[4]  
BENNES RM, 2000, THESIS U BIRMINGHAM
[5]   Efficient recognition-induced acceleration of a [3+2] dipolar cycloaddition reaction [J].
Booth, CA ;
Philp, D .
TETRAHEDRON LETTERS, 1998, 39 (38) :6987-6990
[6]  
BOOTH CA, 1998, THESIS U BIRMINGHAM
[7]   Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]heptanes [J].
Chen, ZM ;
Trudell, ML .
CHEMICAL REVIEWS, 1996, 96 (03) :1179-1193
[8]   HIGH-PRESSURE SYNTHESIS, STRUCTURES, AND CONFORMATIONAL PROPERTIES OF SOME DERIVATIVES OF 7-AZABICYCLO[2.2.1]HEPTANE - X-RAY DETERMINATION OF ENDO-10-BENZOYL-4-PHENYL-4,10-DIAZATRICYCLO[5.2.1.02,6]DEC-8-ENE-3,5-DIONE AND EXO-10-ACETYL-4-PHENYL-4,10-DIAZATRICYCLO[5.2.1.02,6]DECANE-3,5-DIONE [J].
DREW, MGB ;
GEORGE, AV ;
ISAACS, NS ;
RZEPA, HS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07) :1277-1284
[9]   SYNTHESIS OF A NOVEL N-HYDROXYPYRROLE VIA LITHIUM PERCHLORATE ACCELERATED DIELS-ALDER METHODOLOGY [J].
HEARD, NE ;
TURNER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4302-4304
[10]   HIGH-PRESSURE ORGANIC-CHEMISTRY .7. HIGH-PRESSURE REACTIONS OF PYRROLES WITH DIMETHYL ACETYLENEDICARBOXYLATE [J].
KOTSUKI, H ;
MORI, Y ;
NISHIZAWA, H ;
OCHI, M ;
MATSUOKA, K .
HETEROCYCLES, 1982, 19 (10) :1915-1920