Practical synthesis of chiral ligands for catalytic enantioselective cyanosilylation of ketones and ketoimines

被引:33
作者
Kato, N [1 ]
Tomita, D [1 ]
Maki, K [1 ]
Kanai, M [1 ]
Shibasaki, M [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1021/jo049258o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical synthesis of chiral ligands that are useful for catalytic enantioselective cyanosilylation of ketones and ketoimines is described. Compared with the previous synthetic route, the number of total steps is decreased and the total yield is greatly improved. Furthermore, both (+)- and (-)-ligands are readily available by this new synthetic route.
引用
收藏
页码:6128 / 6130
页数:3
相关论文
共 35 条
[1]   The asymmetric addition of trimethylsilyl cyanide to aldehydes catalyzed by chiral (salen)titanium complexes [J].
Belokon, YN ;
Caveda-Cepas, S ;
Green, B ;
Ikonnikov, NS ;
Krustalev, VN ;
Larichev, VS ;
Moscalenko, MA ;
North, M ;
Orizu, C ;
Tararov, VI ;
Tasinazzo, M ;
Timofeeva, GI ;
Yashkina, LV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :3968-3973
[2]   Optimized catalysts for the asymmetric addition of trimethylsilyl cyanide to aldehydes and ketones [J].
Belokon, YN ;
Green, B ;
Ikonnikov, NS ;
North, M ;
Parsons, T ;
Tararov, VI .
TETRAHEDRON, 2001, 57 (04) :771-779
[3]  
Belokon' YN, 2000, EUR J ORG CHEM, V2000, P2655
[4]  
BELOKON YN, 1999, TETRAHEDRON LETT, V38, P6669
[5]   Sc(BINOL)2Li:: a new heterobimetallic catalyst for the asymmetric Strecker reaction [J].
Chavarot, M ;
Byrne, JJ ;
Chavant, PY ;
Vallée, Y .
TETRAHEDRON-ASYMMETRY, 2001, 12 (08) :1147-1150
[6]   Enantioselective cyanosilylation of ketones by a catalytic double-activation method employing chiral Lewis acid and achiral N-oxide catalysts [J].
Chen, FX ;
Feng, XM ;
Qin, B ;
Zhang, GL ;
Jiang, YZ .
ORGANIC LETTERS, 2003, 5 (06) :949-952
[7]  
Deng HB, 2002, ANGEW CHEM INT EDIT, V41, P1009, DOI 10.1002/1521-3773(20020315)41:6<1009::AID-ANIE1009>3.0.CO
[8]  
2-F
[9]   CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX [J].
FU, GC ;
NGUYEN, ST ;
GRUBBS, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9856-9857
[10]   Formal catalytic asymmetric total synthesis of fostriecin [J].
Fujii, K ;
Maki, K ;
Kanai, M ;
Shibasaki, M .
ORGANIC LETTERS, 2003, 5 (05) :733-736