Catalytic enantioselective synthesis of oxindoles and benzofuranones that bear a quaternary stereocenter

被引:235
作者
Hills, ID [1 ]
Fu, GC [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
asymmetric synthesis; heterocycles; homogeneous catalysis; ion pairs; rearrangements;
D O I
10.1002/anie.200351666
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A common feature in indole- and benzofuran-derived natural products is a quaternary stereocenter in the 3-position of the heterocycle. The catalyst (-) -1 promotes the asymmetric synthesis of such compounds 3 (with up to 99% ee) through the rearrangement of O-acylated benzofuranones (X = O) and oxindoles (X = NR2) 2.
引用
收藏
页码:3921 / 3924
页数:4
相关论文
共 38 条
[1]  
Arai S, 2001, ANGEW CHEM INT EDIT, V40, P234, DOI 10.1002/1521-3773(20010105)40:1<234::AID-ANIE234>3.0.CO
[2]  
2-K
[3]  
Arai S., 2001, ANGEW CHEM, V113, P240
[4]   A NOVEL OXYGEN-TO-CARBON ESTER MIGRATION CATALYZED BY 4-(N,N-DIMETHYLAMINO)-PYRIDINE IN THE BENZOFURANONE RING-SYSTEM [J].
BLACK, TH ;
ARRIVO, SM ;
SCHUMM, JS ;
KNOBELOCH, JM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (20) :1524-1525
[5]   4-(DIMETHYLAMINO)PYRIDINE AS A CATALYST FOR CARBON ACYLATION .2. CONTROL OF CARBON VS OXYGEN ACYLATION IN BENZOFURANONES [J].
BLACK, TH ;
ARRIVO, SM ;
SCHUMM, JS ;
KNOBELOCH, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5425-5430
[6]  
Carreira, 2002, ANGEW CHEM, V114, P2601
[7]  
Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO
[8]  
2-V
[9]  
Christoffers J., 2001, ANGEW CHEM, V113, P4725, DOI DOI 10.1002/1521-3757(20011217)113:24
[10]  
Corey E. J., 1998, ANGEW CHEM, V110, P402