Practical highly enantioselective synthesis of terminal propargylamines.: An expeditious synthesis of (S)-(+)-coniine

被引:112
作者
Gommermann, N [1 ]
Knochel, P [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
关键词
D O I
10.1039/b409951f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The one-pot three-component addition reaction of trimethylsilylacetylene, aldehydes and dibenzylamine provides in the presence of CuBr/Quinap as catalyst, various enantiomerically enriched propargylamines in good yields (up to 99%) and excellent enantiomeric excess (up to 98% ee) which can be used as a key intermediate in the synthesis of the alkaloid (S)-(+)-coniine.
引用
收藏
页码:2324 / 2325
页数:2
相关论文
共 40 条
[1]   Electron and proton reservoir complexes: Thermodynamic basis for C-H activation and applications in redox and dendrimer chemistry [J].
Astruc, D .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :287-298
[2]   A new asymmetric synthesis of (S)-(+)-pipecoline and (S)-(+)- and (R)-(-)-coniine by reductive photocyclization of dienamides [J].
Bois, F ;
Gardette, D ;
Gramain, JC .
TETRAHEDRON LETTERS, 2000, 41 (45) :8769-8772
[3]   Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis [J].
Chippindale, AM ;
Davies, SG ;
Iwamoto, K ;
Parkin, RM ;
Smethurst, CAP ;
Smith, AD ;
Rodriguez-Solla, H .
TETRAHEDRON, 2003, 59 (18) :3253-3265
[4]   Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].
Davies, HML ;
Beckwith, REJ .
CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903
[5]  
Doye S, 2001, ANGEW CHEM INT EDIT, V40, P3351, DOI 10.1002/1521-3773(20010917)40:18<3351::AID-ANIE3351>3.0.CO
[6]  
2-B
[7]  
Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
[8]  
2-6
[9]  
DYKER G, 1998, TRANSITION METALS OR, P241
[10]  
ENDERS D, 1993, LIEBIGS ANN CHEM, P173