Asymmetric direct α,β-functionalization of allenes via asymmetric carbopalladation

被引:29
作者
Hiroi, K [1 ]
Kato, F [1 ]
Yamagata, A [1 ]
机构
[1] Tohoku Coll Pharm, Dept Synthet Organ Chem, Sendai, Miyagi 9818558, Japan
关键词
D O I
10.1246/cl.1998.397
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric direct a,p-functionalization of allenes with chiral phosphine ligands was successfully achieved with extremely high enantioselectivity via asymmetric carbopalladation to the racemic allenes. The same palladium-catalyzed alkylation of a chiral allene was executed with complete enantiospecificity. The stereochemistry of this reaction was determined and the mechanism of this asymmetric induction is proposed.
引用
收藏
页码:397 / 398
页数:2
相关论文
共 9 条
[1]  
AHAMAR M, 1987, TETRAHEDRON, V43, P513
[2]   SYNTHESIS OF 1,3-DIENES AND FUNCTIONALIZED STYRENES BY CATALYTIC CARBOPALLADATION OF ALLENES [J].
AHMAR, M ;
CAZES, B ;
GORE, J .
TETRAHEDRON LETTERS, 1984, 25 (40) :4505-4508
[3]   CARBOPALLADATION OF FUNCTIONALIZED ALLENES - REGIOSELECTIVITY OF THE REACTION OF CARBONUCLEOPHILES WITH THE INTERMEDIATE PI-ALLYL PALLADIUM COMPLEXES [J].
CHAPTAL, N ;
COLOVRAYGOTTELAND, V ;
GRANDJEAN, C ;
CAZES, B ;
GORE, J .
TETRAHEDRON LETTERS, 1991, 32 (15) :1795-1798
[4]   ABSOLUTE STERIC COURSE OF HYDROLYSIS BY ALPHA-CHYMOTRYPSIN . ESTERS OF ALPHA-BENZYLSUCCINIC ALPHA-METHYL-BETA-PHENYLPROPIONIC AND ALPHA-METHYLSUCCINIC ACIDS [J].
COHEN, SG ;
MILOVANOVIC, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (13) :3495-+
[5]   VINYL TRIFLUOROSULFONATES IN THE CARBOPALLADATION OF ALLENIC HYDROCARBONS [J].
FRIESS, B ;
CAZES, B ;
GORE, J .
TETRAHEDRON LETTERS, 1988, 29 (33) :4089-4092
[6]  
HIROI K, 1996, TOHOKU YAKKADAIGAKU, V43, P1
[7]   Asymmetric hydrogenation [J].
Noyori, R .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (04) :380-390
[8]  
Ojima I., 2010, CATALYTIC ASYMMETRIC
[9]   ALLENES AND ACETYLENES .21. LEAVING-GROUP EFFECTS ON THE STEREOCHEMISTRY OF ALLENE-FORMING ORGANOCUPRATE REACTIONS [J].
OLSSON, LI ;
CLAESSON, A .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (09) :679-684