Enantioselective nucleophilic substitution of a 6,6-bicyclic dienyl acetate by palladium-chiral phosphine catalyst

被引:14
作者
Shimizu, I [1 ]
Matsumoto, Y [1 ]
Nishikawa, M [1 ]
Kawahara, T [1 ]
Satake, A [1 ]
Yamamoto, A [1 ]
机构
[1] Waseda Univ, Sch Sci & Engn, Dept Appl Chem, Shinjuku Ku, Tokyo 1698555, Japan
关键词
D O I
10.1246/cl.1998.983
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective nucleophilic substitution of (+/-)-2 beta-acetoxy-4a beta-methyl-2,3,4,4a, 5,6-hexahydronaphthalene with dimethyl malonate anion was performed in the presence of palladium-chiral ligand catalysts to give optically active 2-di(methoxycarbonyl)methyl-4a-methyl-2,3,4,4a,5, 6-hexahydronaphthalenes.
引用
收藏
页码:983 / 984
页数:2
相关论文
共 30 条
[11]  
Noyori R., 1994, ASYMMETRIC CATALYSIS
[12]  
Ojima I., 2010, CATALYTIC ASYMMETRIC
[13]   CHIRAL SEMICORRINS AND RELATED NITROGEN-HETEROCYCLES AS LIGANDS IN ASYMMETRIC CATALYSIS [J].
PFALTZ, A .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (06) :339-345
[14]  
REISER O, 1993, ANGEW CHEM INT EDIT, V32, P547, DOI 10.1002/anie.199305471
[15]   PHOSPHINOARYLOXAZOLINES AND PHOSPHINOALKYLOXAZOLINES AS NEW CHIRAL LIGANDS FOR ENANTIOSELECTIVE CATALYSIS - VERY HIGH ENANTIOSELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTIONS [J].
SPRINZ, J ;
HELMCHEN, G .
TETRAHEDRON LETTERS, 1993, 34 (11) :1769-1772
[16]   THE 1ST OBSERVATION OF SYN-ANTI DICHOTOMY IN THE FORMATION OF (PI-ALLYL)PALLADIUM COMPLEXES [J].
STARY, I ;
KOCOVSKY, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4981-4982
[17]   ON THE NATURE OF THE ION-PAIR AS A NUCLEOPHILE IN PD CATALYZED ALKYLATIONS WITH DIENYL CARBOXYLATES [J].
TROST, BM ;
BUNT, RC .
TETRAHEDRON LETTERS, 1993, 34 (47) :7513-7516
[18]   Asymmetric transition metal-catalyzed allylic alkylations [J].
Trost, BM ;
VanVranken, DL .
CHEMICAL REVIEWS, 1996, 96 (01) :395-422
[19]   REGIOCHEMICAL DIRECTING EFFECTS IN PALLADIUM CATALYZED ALKYLATIONS WITH POLYENE ELECTROPHILIC PARTNERS [J].
TROST, BM ;
URCH, CJ ;
HUNG, MH .
TETRAHEDRON LETTERS, 1986, 27 (41) :4949-4952
[20]   ON THE REGIOCHEMISTRY OF METAL-CATALYZED ALLYLIC ALKYLATION - A MODEL [J].
TROST, BM ;
HUNG, MH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (22) :6837-6839