Direct catalytic asymmetric aldol reactions promoted by novel heterobimetallic catalysts possessing strong Bronsted base: a new strategy for the development of Lewis acid-Bronsted base bifunctional catalysts

被引:59
作者
Yoshikawa, N [1 ]
Shibasaki, M [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
基金
日本学术振兴会;
关键词
direct catalytic asymmetric aldol reaction; lanthanide; heterobimetallic multifunctional catalyst;
D O I
10.1016/S0040-4020(01)00070-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel heterobimetallic catalysts possessing lithium alkoxide as Bronsted base have been developed. The catalysts were found to be effective in the direct asymmetric aldol reaction of less acidic dialkyl ketones as well as aromatic ketones, affording the aldol products in moderate yield and ee. Attempts at diastereo- and enantioselective direct catalytic aldol reaction of ethyl ketone using small molecule catalysts are reported for the first time. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:2569 / 2579
页数:11
相关论文
共 49 条
[1]   FLUORIDE SALTS ON ALUMINA AS REAGENTS FOR ALKYLATION OF PHENOLS AND ALCOHOLS [J].
ANDO, T ;
YAMAWAKI, J ;
KAWATE, T ;
SUMI, S ;
HANAFUSA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (08) :2504-2507
[2]   CERIUM CHLORIDE(III) PROMOTED NUCLEOPHILIC-ADDITION OF ORGANOLITHIUM REAGENTS TO ALPHA-DIPHENYLPHOSPHINOYL KETONES - AN EFFICIENT METHOD FOR THE SYNTHESIS OF HORNER-WITTIG INTERMEDIATES [J].
BARTOLI, G ;
SAMBRI, L ;
MARCANTONI, E ;
PETRINI, M .
TETRAHEDRON LETTERS, 1994, 35 (45) :8453-8456
[3]   Chiral triarylcarbenium ions in asymmetric Mukaiyama aldol additions [J].
Chen, CT ;
Chao, SD ;
Yen, KC ;
Chen, CH ;
Chou, IC ;
Hon, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) :11341-11342
[4]   ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].
COREY, EJ ;
CYWIN, CL ;
ROPER, TD .
TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910
[5]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[6]   Chiral phosphoramide-catalyzed aldol additions of ketone enolates. Preparative aspects [J].
Denmark, SE ;
Stavenger, RA ;
Wong, KT ;
Su, XP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :4982-4991
[7]   MECHANISM AND SYNTHETIC UTILITY OF BORON-TRIFLUORIDE ETHERATE PROMOTED ORGANO-LITHIUM ADDITIONS [J].
EIS, MJ ;
WROBEL, JE ;
GANEM, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) :3693-3694
[8]   C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde [J].
Evans, DA ;
Kozlowski, MC ;
Murry, JA ;
Burgey, CS ;
Campos, KR ;
Connell, BT ;
Staples, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :669-685
[9]   C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of the catalytic enantioselective aldol additions of enolsilanes to pyruvate esters [J].
Evans, DA ;
Burgey, CS ;
Kozlowski, MC ;
Tregay, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :686-699
[10]   CATALYTIC ASYMMETRIC ALDOL REACTIONS - USE OF A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS ACID CATALYST [J].
FURUTA, K ;
MARUYAMA, T ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1041-1042