TBD-catalyzed cyanosilylation of aldehydes and ketones

被引：7

作者：

Matsukawa, S. ^{[1
]}

Kimura, J. ^{[1
]}

机构：

[1] Ibaraki Univ, Dept Sci Educ, Fac Educ, Mito, Ibaraki 3108512, Japan

来源：

SYNTHETIC COMMUNICATIONS | 2016年 / 46卷 / 23期

关键词：

Base catalyst; cyanosilylation; guanidine; organocatalyst; CYANOHYDRIN TRIMETHYLSILYL ETHERS; EFFICIENT CATALYSTS; CARBONYL-COMPOUNDS; N-OXIDE; CYANIDE; ORGANOCATALYST; KETOALDEHYDES; ACTIVATION; CYANATION; TMSCN;

D O I：

10.1080/00397911.2016.1241884

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This study examines the catalytic efficacy of 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) in the cyanosilylation of aldehydes and ketones. In an aldehyde reaction, the corresponding products were obtained at high yield using minimal TBD (0.01mol%). TBD was similarly effective in various ketone reactions.

引用

页码：1947 / 1952

页数：6

共 44 条

[1] Tetrabutylammonium cyanide catalyzed diasteroselective cyanosliylation of chiral α-hydroxyketones [J].

Amurrio, I ;

Córdoba, R ;

Csákÿ, AG ;

Plumet, J .

TETRAHEDRON, 2004, 60 (46) :10521-10524

[2] Solvent-free synthesis of cyanohydrin derivatives catalysed by triethylamine [J].

Baeza, A ;

Nájera, C ;

Retamosa, MD ;

Sansano, JM .

SYNTHESIS-STUTTGART, 2005, (16) :2787-2797

[3] Chemically catalyzed asymmetric cyanohydrin syntheses [J].

Brunel, JM ;

Holmes, IP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (21) :2752-2778

[4] Synthesis of racemic tertiary cyanohydrins [J].

Chen, FX ;

Feng, XM .

SYNLETT, 2005, (06) :892-899

[5] Bicyclic-guanidines, -guanidinates and -guanidinium salts: wide ranging applications from a simple family of molecules [J].

Coles, Martyn P. .

CHEMICAL COMMUNICATIONS, 2009, (25) :3659-3676

[6] Methyltriphenylphosphonium iodide catalyzes the addition of trimethylsilyl cyanide to aldehydes [J].

Córdoba, R ;

Plumet, J .

TETRAHEDRON LETTERS, 2003, 44 (32) :6157-6159

[7] Organocatalytic cyanosilylation of carbonyl compounds by tetrabutylammonium phthalimide-N-oxyl [J].

Dekamin, Mohammad G. ;

Mokhtari, Javad ;

Naimi-Jamal, M. Reza .

CATALYSIS COMMUNICATIONS, 2009, 10 (05) :582-585

[8] An expeditious synthesis of cyanohydrin trimethylsilyl ethers using tetraethylammonium 2-(carbamoyl)benzoate as a bifunctional organocatalyst [J].

Dekamin, Mohammad G. ;

Sagheb-Asl, Solmaz ;

Naimi-Jamal, M. Reza .

TETRAHEDRON LETTERS, 2009, 50 (28) :4063-4066

[9] Lewis base catalyzed addition of trimethylsilyl cyanide to aldehydes [J].

Denmark, SE ;

Chung, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (10) :4002-4005

[10] Highly syn-diastereoselective Michael addition of enolizable ketones to 3-(diethoxyphosphoryl)coumarin [J].

Deredas, Dariusz ;

Huben, Krzysztof ;

Maniukiewicz, Waldemar ;

Krawczyk, Henryk .

TETRAHEDRON, 2014, 70 (46) :8925-8929

← 1 2 3 4 5 →