Me-bipam for Enantioselective Ruthenium (II)-Catalyzed Arylation of Aldehydes with Arylboronic Acids

被引:120
作者
Yamamoto, Yasunori [1 ]
Kurihara, Kazunori [1 ]
Miyaura, Norio [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan
关键词
aldehydes; asymmetric catalysis; boron; nucleophilic addition; ruthenium; RHODIUM-CATALYZED ADDITION; CARBONYL-COMPOUNDS; ALPHA; BETA-UNSATURATED KETONES; ASYMMETRIC-SYNTHESIS; ORGANOBORONIC ACIDS; AROMATIC-ALDEHYDES; 1,2-ADDITION; 1,4-ADDITION; COMPLEXES; ARYL;
D O I
10.1002/anie.200901395
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ligand design by-pam: A ruthenium-catalyzed asymmetric arylation of aldehydes with arylboronic acids has been developed, giving chiral diarylmethanols in good yields. The use of a chiral bidentate phosphoramidite ligand ((R,R)-Me-bipam) led to excellent enantioselectivities. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4414 / 4416
页数:3
相关论文
共 63 条
[1]   Nickel-catalyzed 1,2-addition of arylboroxines to aromatic aldehydes [J].
Arao, Takafumi ;
Kondo, Kazuhiro ;
Aoyama, Toyohiko .
TETRAHEDRON LETTERS, 2007, 48 (23) :4115-4117
[2]   Asymmetric synthesis of diarylmethanols: Development of a hemilabile phosphorus ligand based on the concept of conformational control [J].
Arao, Takafumi ;
Suzuki, Kiyoto ;
Kondo, Kazuhiro ;
Aoyama, Toyobiko .
SYNTHESIS-STUTTGART, 2006, (22) :3809-3814
[3]   PREPARATION, AND MECHANISM OF FORMATION, OF ALKYL AND PHENYL COMPLEXES OF RUTHENIUM(2) [J].
BARNARD, CFJ ;
DANIELS, JA ;
MAWBY, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1976, (11) :961-966
[4]   Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
ORGANIC LETTERS, 1999, 1 (10) :1683-1686
[5]  
BROWN JM, 1995, COMPREHENSIVE ORGANO, V11, P129
[6]   REACTIONS OF CHLOROHYDRIDO AND DICHLORO-TRIS(TRIPHENYLPHOSPHINE)-RUTHENIUM(II) WITH ALKALI HYDROXIDES AND ALKOXIDES - HYDRIDOHYDROXOBIS-(TRIPHENYLPHOSPHINE)RUTHENIUM(II) MONOSOLVATES, THEIR REACTIONS AND RELATED COMPOUNDS [J].
CHAUDRET, BN ;
COLEHAMILTON, DJ ;
NOHR, RS ;
WILKINSON, G .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1977, (16) :1546-1557
[7]   Enantioselective rhodium-catalyzed addition of arylboronic acids to aldehydes using chiral spiro monophosphite ligands [J].
Duan, HF ;
Xie, JH ;
Shi, WJ ;
Zhang, Q ;
Zhou, QL .
ORGANIC LETTERS, 2006, 8 (07) :1479-1481
[8]  
Farrington E.J., 2002, ANGEW CHEM, V114, P177
[9]   Ruthenium complex-catalysed Heck reactions of areneboronic acids; Mechanism, synthesis and halide tolerance [J].
Farrington, EJ ;
Barnard, CFJ ;
Rowsell, E ;
Brown, JM .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (01) :185-195
[10]  
Farrington EJ, 2002, ANGEW CHEM INT EDIT, V41, P169, DOI 10.1002/1521-3773(20020104)41:1<169::AID-ANIE169>3.0.CO