Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3′-oxoindoles

被引:160
作者
Bella, M [1 ]
Kobbelgaard, S [1 ]
Jorgensen, KA [1 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus, Denmark
关键词
D O I
10.1021/ja050200g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first example of catalytic enantioselective nucleophilic aromatic substitution of -dicarbonyl compounds is presented. An O-benzoylated cinchona alkaloid derivative catalyst gave a selective C-arylation reaction compared to, e.g., the corresponding benzylated catalyst which provided a 1:1 mixture of the C- and O-arylation products. The reaction proceeds well for various aromatic compounds with different 1,3-dicarbonyl compounds, and the optically active products are obtained in very high yields and with up to 92% ee. One further scope of the organocatalytic enantioselective nucleophilic aromatic substitution reaction is demonstrated by the synthesis of the optically active spiro-pyrrolidone-3,3′-oxoindole structure. Copyright © 2005 American Chemical Society.
引用
收藏
页码:3670 / 3671
页数:2
相关论文
共 33 条
[1]  
[Anonymous], 1997, PHASE TRANSFER CATAL
[2]   Organocatalytic enantioselective conjugate addition to alkynones [J].
Bella, M ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5672-5673
[3]   RATIONALIZING THE REGIOSELECTIVITY IN POLYNITROARENE ANIONIC SIGMA-ADDUCT FORMATION - RELEVANCE TO NUCLEOPHILIC AROMATIC-SUBSTITUTION [J].
BUNCEL, E ;
DUST, JM ;
TERRIER, F .
CHEMICAL REVIEWS, 1995, 95 (07) :2261-2280
[4]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[5]  
2-V
[6]   ASYMMETRIC INDUCTION IN THE MICHAEL REACTION BY MEANS OF CHIRAL PHASE-TRANSFER CATALYSTS DERIVED FROM CINCHONA AND EPHEDRA ALKALOIDS [J].
COLONNA, S ;
RE, A ;
WYNBERG, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (02) :547-552
[7]   Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism [J].
Corey, EJ ;
Bo, YX ;
Busch-Petersen, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :13000-13001
[8]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[9]  
2-V
[10]   EFFICIENT CATALYTIC ASYMMETRIC ALKYLATIONS .1. ENANTIOSELECTIVE SYNTHESIS OF (+)-INDACRINONE VIA CHIRAL PHASE-TRANSFER CATALYSIS [J].
DOLLING, UH ;
DAVIS, P ;
GRABOWSKI, EJJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) :446-447