Function of an N-heterocyclic carbene ligand based on concept of chiral mimetic

被引:35
作者
Arao, Takafumi [1 ]
Sato, Kei [1 ]
Kondo, Kazuhiro [1 ]
Aoyama, Toyohiko [1 ]
机构
[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
关键词
optically active N-heterocyclic carbene ligand; chiral mimetic; imidazolium salt; asymmetric arylation;
D O I
10.1248/cpb.54.1576
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Function of a new N-heterocyclic carbene ligand based on the concept of a chiral mimetic is described. With (4R,5R)-4,5-diphenyl-1,3-dialkyl-4,5-dihydro-3H-imidazol-1-ium tetrafluoroborates as N-heterocyclic carbene precursors, Rh-catalyzed enantioselective arylation (up to 27% ee) of aromatic aldehydes with arylboronic acids and Pd-catalyzed enantioselective intramolecular alpha-arylation (up to 66% ee) of N-(2-bromoaryl)-N-alkyl-2-arylpropanamides are investigated.
引用
收藏
页码:1576 / 1581
页数:6
相关论文
共 31 条
[1]   Development of an N-heterocyclic carbene ligand based on concept of chiral mimetic [J].
Arao, T ;
Kondo, K ;
Aoyama, T .
TETRAHEDRON LETTERS, 2006, 47 (09) :1417-1420
[2]  
ARAO T, 2006, IN PRESS SYNTHESIS
[3]   Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis [J].
César, V ;
Bellemin-Laponnaz, S ;
Gade, LH .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :619-636
[4]   Planar chiral imidazolium salts in the asymmetric rhodium-catalyzed 1,2-addition of arylboronic acids to aldehydes [J].
Focken, T ;
Rudolph, J ;
Bolm, C .
SYNTHESIS-STUTTGART, 2005, (03) :429-436
[5]  
Fürstner A, 2001, ADV SYNTH CATAL, V343, P343
[6]   Oxazolines as chiral building blocks for imidazolium salts and N-heterocyclic carbene ligands [J].
Glorius, F ;
Altenhoff, G ;
Goddard, R ;
Lehmann, C .
CHEMICAL COMMUNICATIONS, 2002, (22) :2704-+
[7]   Palladium-catalyzed direct α-arylation of ketones.: Rate acceleration by sterically hindered chelating ligands and reductive elimination from a transition metal enolate complex [J].
Hamann, BC ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12382-12383
[8]  
Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO
[9]  
2-Y
[10]   Asymmetric Kumada-Corriu cross-coupling reaction with Pd2(dba)3 and an N-Ar axially chiral mimetic-type ligand catalyst [J].
Hideo, H ;
Fukuda, Y ;
Kondo, K ;
Okuno, H ;
Murakami, Y ;
Aoyama, T .
TETRAHEDRON, 2004, 60 (47) :10701-10709