TiCl(OiPr)3 and NaBH(OAc)3:: an efficient reagent combination for the reductive amination of aldehydes by electron-deficient amines

被引：40

作者：

Gutierrez, CD ^{[1
]}

Bavetsias, V ^{[1
]}

McDonald, E ^{[1
]}

机构：

[1] Canc Res UK, Ctr Canc Therapeut, Inst Canc Res, Dept Chem,Canc Res UK Lab, Sutton SM2 5NG, Surrey, England

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 20期

关键词：

D O I：

10.1016/j.tetlet.2005.02.155

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sodium triacetoxyborohydride, NaBH(OAC)(3) with tri-isopropoxytitanium chloride, TiCl((OPr)-Pr-i)(3) is a useful reagent combination for reductive amination. Electron-deficient amines and heteroaromatic amines such as 2-aminopyrimidine and 2-aminothiazole can be reductively alkylated at room temperature to afford the corresponding secondary amines in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

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页码：3595 / 3597

页数：3

相关论文

共 16 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2]

Atrash B, 2001, ANGEW CHEM INT EDIT, V40, P938, DOI 10.1002/1521-3773(20010302)40:5<938::AID-ANIE938>3.3.CO

[3]

2-3

[4]

Bae JW, 2000, J CHEM SOC PERK T 1, P145

[5] A MILD, PYRIDINE-BORANE-BASED REDUCTIVE AMINATION PROTOCOL [J].

BOMANN, MD ;

GUCH, IC ;

DIMARE, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5995-5996

[6] Titanium mediated reductive amination on solid support: Extending the utility of the 4-hydroxy-thiophenol linker [J].

Breitenbucher, JG ;

Hui, HC .

TETRAHEDRON LETTERS, 1998, 39 (45) :8207-8210

[7] Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin™ approach [J].

Bui, CT ;

Bray, AM ;

Pham, Y ;

Campbell, R ;

Ercole, F ;

Rasoul, FA ;

Maeji, NJ .

MOLECULAR DIVERSITY, 1998, 4 (03) :155-163

[8] A versatile solid phase synthesis of lavendustin A and certain biologically active analogs [J].

Devraj, R ;

Cushman, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9368-9373

[9] AMEBA: An acid sensitive aldehyde resin for solid phase synthesis [J].

Fivush, AM ;

Willson, TM .

TETRAHEDRON LETTERS, 1997, 38 (41) :7151-7154

[10] REDUCTIVE ALKYLATION ON A SOLID-PHASE - SYNTHESIS OF A PIPERAZINEDIONE COMBINATORIAL LIBRARY [J].

GORDON, DW ;

STEELE, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (01) :47-50