Nickel-catalyzed 1,2-addition of arylboroxines to aromatic aldehydes

被引：61

作者：

Arao, Takafumi ^{[1
]}

Kondo, Kazuhiro ^{[1
]}

Aoyama, Toyohiko ^{[1
]}

机构：

[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 23期

关键词：

nickel; arylation; 1,2-addition; boroxine; aldehyde; Duphos;

D O I：

10.1016/j.tetlet.2007.04.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Development of Ni-Et-Duphos-catalyzed 1,2-addition of arylboroxines to aromatic aldehydes is described. The dramatic effect of boron reagent and phosphine ligand is observed. This method with a phosphine ligand allows asymmetric arylation of aromatic aldehydes (up to 78% ee). (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：4115 / 4117

页数：3

共 24 条

[1] Function of an N-heterocyclic carbene ligand based on concept of chiral mimetic [J].

Arao, Takafumi ;

Sato, Kei ;

Kondo, Kazuhiro ;

Aoyama, Toyohiko .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (11) :1576-1581

[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] Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source [J].

Bolm, C ;

Rudolph, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14850-14851

[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] Nickel-catalyzed alkylation of aldehydes with trialkylboranes [J].

Hirano, K ;

Yorimitsu, H ;

Oshima, K .

ORGANIC LETTERS, 2005, 7 (21) :4689-4691

[7] Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes [J].

Mahandru, GM ;

Liu, G ;

Montgomery, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3698-3699

[8] Catalytic asymmetric reductive coupling of alkynes and aldehydes:: Enantioselective synthesis of allylic alcohols and α-hydroxy ketones [J].

Miller, KM ;

Huang, WS ;

Jamison, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) :3442-3443

[9] Rhodium-catalysed aryl transfer to aldehydes: counterion effects with nitrogen containing ligands [J].

Moreau, C ;

Hague, C ;

Weller, AS ;

Frost, CG .

TETRAHEDRON LETTERS, 2001, 42 (39) :6957-6960

[10] Direct observation of oxidative Cyclization of η2-alkene and η2-aldehyde on Ni(0) center.: Significant acceleration by addition of Me3SiOTf [J].

Ogoshi, S ;

Oka, M ;

Kurosawa, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11802-11803

← 1 2 3 →