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

被引：110

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

页码：429 / 436

页数：8

共 88 条

[1] Asymmetric synthesis with N-heterocyclic carbenes.: Application to the copper-catalyzed conjugate addition
Alexakis, A
Winn, CL
Guillen, F
Pytkowicz, J
Roland, S
Mangeney, P
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (03) : 345 - 348
[2] Synthesis and application of complexes of a novel chiral diphenylphosphino-functionalized N-heterocyclic carbene
Bappert, E
Helmchen, G
[J]. SYNLETT, 2004, (10) : 1789 - 1793
[3] Synthesis of iridium complexes with novel planar chiral chelating imidazolylidene ligands
Bolm, C
Focken, T
Raabe, G
[J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (12) : 1733 - 1746
[4] The first planar-chiral stable carbene and its metal complexes
Bolm, C
Kesselgruber, M
Raabe, G
[J]. ORGANOMETALLICS, 2002, 21 (04) : 707 - 710
[5] Catalytic enantioselective aryl transfer:: asymmetric addition of diphenylzinc to aldehydes
Bolm, C
Muñiz, K
[J]. 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
Bolm, C
Kesselgruber, M
Grenz, A
Hermanns, N
Hildebrand, JP
[J]. 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
Bolm, C
Hermanns, N
Kesselgruber, M
Hildebrand, JP
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 157 - 161
[10] Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285

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