Planar chiral imidazolium salts in the asymmetric rhodium-catalyzed 1,2-addition of arylboronic acids to aldehydes

被引：112
作者：
Focken, T [1 ]
Rudolph, J [1 ]
Bolm, C [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
来源：
SYNTHESIS-STUTTGART | 2005年 / 03期
关键词：
2.2]paracyclophane; N-heterocyclic carbene; imidazolium salt; asymmetric catalysis; boronic acid; diarylmethanol;
D O I：
10.1055/s-2005-861800
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Planar chiral imidazolium salts 8 and 13 were used as precursors for N-heterocyclic carbene ligands, which were applied in rhodium-catalyzed additions of arylboronic acids to aromatic aldehydes. With pseudo-ortho-disubstituted [2.2]paracyclophane (S,R-p)-8b bearing a phosphinoyl substituent at the paracyclophane backbone, 38% ee has been achieved in this rather unexplored reaction.
引用
收藏
页码：429 / 436
页数：8
相关论文
共 88 条
[1]   Asymmetric synthesis with N-heterocyclic carbenes.: Application to the copper-catalyzed conjugate addition [J].
Alexakis, A ;
Winn, CL ;
Guillen, F ;
Pytkowicz, J ;
Roland, S ;
Mangeney, P .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (03) :345-348
[2]   Synthesis and application of complexes of a novel chiral diphenylphosphino-functionalized N-heterocyclic carbene [J].
Bappert, E ;
Helmchen, G .
SYNLETT, 2004, (10) :1789-1793
[3]   Synthesis of iridium complexes with novel planar chiral chelating imidazolylidene ligands [J].
Bolm, C ;
Focken, T ;
Raabe, G .
TETRAHEDRON-ASYMMETRY, 2003, 14 (12) :1733-1746
[4]   The first planar-chiral stable carbene and its metal complexes [J].
Bolm, C ;
Kesselgruber, M ;
Raabe, G .
ORGANOMETALLICS, 2002, 21 (04) :707-710
[5]   Catalytic enantioselective aryl transfer:: asymmetric addition of diphenylzinc to aldehydes [J].
Bolm, C ;
Muñiz, K .
CHEMICAL COMMUNICATIONS, 1999, (14) :1295-1296
[6]  
Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P1488, DOI 10.1002/1521-3773(20010417)40:8<1488::AID-ANIE1488>3.0.CO
[7]  
2-B
[8]   A novel ferrocenyl diselenide for the catalytic asymmetric aryl transfer to aldehydes [J].
Bolm, C ;
Kesselgruber, M ;
Grenz, A ;
Hermanns, N ;
Hildebrand, JP .
NEW JOURNAL OF CHEMISTRY, 2001, 25 (01) :13-15
[9]   Synthesis of novel 1,1′-bis(oxazolinyl)metallocenes and their application in the asymmetric phenyl transfer from organozincs to aldehydes [J].
Bolm, C ;
Hermanns, N ;
Kesselgruber, M ;
Hildebrand, JP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) :157-161
[10]  
Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
123456789