Chiral Ti(IV) complexes of hexadentate Schiff bases as precatalysts for aldehyde allylation: unusual additive effect of trimethylsilyl chloride

被引：24

作者：

Belokon, Yuri N. ^{[1
]}

Chusov, Denis ^{[1
]}

Borkin, Dinitry A. ^{[1
]}

Yashkina, Lidia V. ^{[1
]}

Bolotov, Pavel ^{[1
]}

Skrupskaya, Tatiana ^{[1
]}

North, Michael ^{[2
,3
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

[2] Univ Newcastle Upon Tyne, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

[3] Univ Newcastle Upon Tyne, Univ Res Ctr Catalysis & intensified Proc, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 04期

基金：

俄罗斯基础研究基金会;

关键词：

D O I：

10.1016/j.tetasy.2008.01.035

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral dinuclear titanium(IV) complexes have been found to be more effective catalysts for the asymmetric allylation of p-nitrobenzaldehyde than their mononuclear analogues. The addition of trimethylsilyl chloride to the reaction mixture decreases the rate of the background reaction and increases the yield of the reaction catalysed by the dinuclear complex. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：459 / 466

页数：8

共 38 条

[1] Synthetic and mechanistic studies on asymmetric cyanohydrin synthesis using a titanium(salen) bimetallic catalyst [J].

Belokon, YN ;

Blacker, AJ ;

Carta, P ;

Clutterbuck, LA ;

North, M .

TETRAHEDRON, 2004, 60 (46) :10433-10447

[2]

Belokon YN, 2002, HELV CHIM ACTA, V85, P3301, DOI 10.1002/1522-2675(200210)85:10<3301::AID-HLCA3301>3.0.CO

[3]

2-2

[4] The asymmetric addition of trimethylsilyl cyanide to aldehydes catalyzed by chiral (salen)titanium complexes [J].

Belokon, YN ;

Caveda-Cepas, S ;

Green, B ;

Ikonnikov, NS ;

Krustalev, VN ;

Larichev, VS ;

Moscalenko, MA ;

North, M ;

Orizu, C ;

Tararov, VI ;

Tasinazzo, M ;

Timofeeva, GI ;

Yashkina, LV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :3968-3973

[5] Chiral Ti(IV) complexes of hexadentate Schiff bases as precatalysts for the asymmetric addition of TMSCN to aldehydes and the ring opening of cyclohexene oxide [J].

Belokon, Yuri N. ;

Chusov, Denis ;

Borkin, Dmitry A. ;

Yashkina, Lidia V. ;

Dmitriev, Andrey V. ;

Katayev, Dmitry ;

North, Michael .

TETRAHEDRON-ASYMMETRY, 2006, 17 (16) :2328-2333

[6] Catalytic asymmetric epoxidation of alpha,beta-unsaturated ketones promoted by lanthanoid complexes [J].

Bougauchi, M ;

Watanabe, S ;

Arai, T ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2329-2330

[7]

BROWN H, 1983, J AM CHEM SOC, V105, P209

[8] ASYMMETRIC CATALYSIS .49. OPTICALLY-ACTIVE BINAPHTHYL DERIVATIVES - SYNTHESIS AND USE IN TRANSITION-METAL CATALYSTS [J].

BRUNNER, H ;

GOLDBRUNNER, J .

CHEMISCHE BERICHTE, 1989, 122 (10) :2005-2009

[9] Enantioselective allylation of aldehydes with allyltrichlorosilane promoted by new chiral dipyridylmethane N-oxides [J].

Chelucci, Giorgio ;

Belmonte, Nicola ;

Benaglia, Maurizio ;

Pignataro, Luca .

TETRAHEDRON LETTERS, 2007, 48 (23) :4037-4041

[10] The application of the formyl C-H--O hydrogen bond postulate to the understanding of enantioselective reactions involving chiral boron Lewis acids and aldehydes [J].

Corey, EJ ;

Rohde, JJ .

TETRAHEDRON LETTERS, 1997, 38 (01) :37-40

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