Bifunctional transition metal-based molecular catalysts for asymmetric syntheses

被引:606
作者
Ikariya, T
Murata, K
Noyori, R
机构
[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
[2] Nagoya Univ, Fac Sci, Dept Chem, Nagoya, Aichi 4648602, Japan
[3] Nagoya Univ, Res Ctr Mat Sci, Nagoya, Aichi 4648602, Japan
关键词
D O I
10.1039/b513564h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The discovery and development of conceptually new chiral bifunctional transition metal-based catalysts for asymmetric reactions is described. The chiral bifunctional Ru catalyst was originally developed for asymmetric transfer hydrogenation of ketones and imines and is now successfully applicable to enantioselective C-C bond formation reaction with a wide scope and high practicability. The deprotonation of 1,3-dicarbonyl compounds with the chiral amido Ru complexes leading to the amine Ru complexes bearing C- or O-bonded enolates, followed by further reactions with electrophlies gives C-C bond formation products. The present bifunctional Ru catalyst offers a great opportunity to open up new fundamentals for stereoselective molecular transformation including enantioselective C-H and C-C as well as C-O, C-N bond formation.
引用
收藏
页码:393 / 406
页数:14
相关论文
共 143 条
[71]   Direct catalytic enantio- and diastereoselective aldol reaction using a Zn-Zn-linked-BINOL complex:: A practical synthesis of syn-1,2-diols [J].
Kumagai, N ;
Matsunaga, S ;
Yoshikawa, N ;
Ohshima, T ;
Shibasaki, M .
ORGANIC LETTERS, 2001, 3 (10) :1539-1542
[72]   Chiral amidomonophosphine-rhodium(I) catalyst for asymmetric 1,4-addition of arylboronic acids to cycloalkenones [J].
Kuriyama, M ;
Tomioka, K .
TETRAHEDRON LETTERS, 2001, 42 (05) :921-923
[73]   Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition [J].
Li, HM ;
Wang, Y ;
Tang, L ;
Wu, FH ;
Liu, XF ;
Guo, CY ;
Foxman, BM ;
Deng, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :105-108
[74]   Highly enantioselective conjugate addition of malonate and β-ketoester to nitroalkenes:: Asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids [J].
Li, HM ;
Wang, Y ;
Tang, L ;
Deng, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) :9906-9907
[75]   Asymmetric transfer hydrogenation in water with a supported Noyori-Ikariya catalyst [J].
Li, XG ;
Wu, XF ;
Chen, WP ;
Hancock, FE ;
King, F ;
Xiao, JL .
ORGANIC LETTERS, 2004, 6 (19) :3321-3324
[76]   Proline-catalyzed direct asymmetric aldol reactions [J].
List, B ;
Lerner, RA ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2395-2396
[77]   Asymmetric aminocatalysis [J].
List, B .
SYNLETT, 2001, (11) :1675-1686
[78]   Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents [J].
List, B .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :548-557
[79]   Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes [J].
List, B ;
Pojarliev, P ;
Castello, C .
ORGANIC LETTERS, 2001, 3 (04) :573-575
[80]   Highly efficient and recyclable heterogeneous asymmetric transfer hydrogenation of ketones in water [J].
Liu, PN ;
Deng, JG ;
Tu, YQ ;
Wang, SH .
CHEMICAL COMMUNICATIONS, 2004, (18) :2070-2071