Palladium-catalyzed asymmetric reduction of allylic esters with a new chiral monodentate ligand, 8-diphenylphosphino-8′-methoxy-1,1′-binaphthyl

被引:39
作者
Fuji, K [1 ]
Sakurai, M
Kinoshita, T
Kawabata, T
机构
[1] Kyoto Univ, Inst Chem Res, Uji, Kyoto 611, Japan
[2] Fujisawa Pharmaceut Co Ltd, Chem Res Labs, Yodogawa Ku, Osaka 532, Japan
[3] Fujisawa Pharmaceut Co Ltd, Basic Res Labs, Yodogawa Ku, Osaka 532, Japan
关键词
asymmetric reactions; hydrogenolysis; phosphines; palladium and compounds;
D O I
10.1016/S0040-4039(98)01342-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new chiral monodentate ligand, 8-diphenylphosphino-8'-methoxy-1,1'-binaphthyl (8-MeO-MOP), was used for palladium-catalyzed reduction of allylic carbonates with formic acid. Various methylcarbonates of 3,3'-disubstituted allylic alcohols were converted to the corresponding optically active 1-olefins with this ligand. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6323 / 6326
页数:4
相关论文
共 16 条
[1]  
FREDGA A, 1955, ARK KEMI, V8, P463
[2]   1,1'-binaphthalene-8,8'-diol as an efficient chiral controller: Highly enantioselective synthesis of optically active ketones [J].
Fuji, K ;
Yang, XS ;
Tanaka, K ;
Asakawa, N ;
Hao, XJ .
TETRAHEDRON LETTERS, 1996, 37 (41) :7373-7376
[3]   ENANTIOSELECTIVE PROTONATION OF ENOLATES - NOVEL CHIRAL PROTON SOURCES AND REMARKABLE EFFECTS OF THE COUNTERCATION [J].
FUJI, K ;
KAWABATA, T ;
KURODA, A ;
TAGA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :1914-1915
[4]   Unexpectedly facile racemization of 8-diphenylphosphinoyl-8'-methoxy-1,1'-binaphthyl [J].
Fuji, K ;
Sakurai, M ;
Tohkai, N ;
Kuroda, A ;
Kawabata, T ;
Fukazawa, Y ;
Kinoshita, T ;
Tada, T .
CHEMICAL COMMUNICATIONS, 1996, (14) :1609-1610
[5]  
Fuji K, 1997, CHEM PHARM BULL, V45, P1524
[6]   CATALYTIC ASYMMETRIC REDUCTION OF ALLYLIC ESTERS WITH FORMIC-ACID CATALYZED BY PALLADIUM MOP COMPLEXES [J].
HAYASHI, T ;
IWAMURA, H ;
NAITO, M ;
MATSUMOTO, Y ;
UOZUMI, Y ;
MIKI, M ;
YANAGI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :775-776
[7]  
HAYASHI T, 1994, SYNTHESIS-STUTTGART, P526
[8]   Catalytic asymmetric synthesis of optically active alkenes by palladium-catalysed asymmetric reduction of racemic allylic esters with formic acid [J].
Hayashi, T ;
Kawatsura, M ;
Iwamura, H ;
Yamaura, Y ;
Uozumi, Y .
CHEMICAL COMMUNICATIONS, 1996, (15) :1767-1768
[10]   Chiral recognition of amino acid derivatives by 1,1'-binaphthalene-8,8'-diol [J].
Kawabata, T ;
Kuroda, A ;
Nakata, E ;
Takasu, K ;
Fuji, K .
TETRAHEDRON LETTERS, 1996, 37 (24) :4153-4156