Highly efficient trialkylsilylcyanation of aldehydes, ketones and imines catalyzed by a nucleophilic N-heterocyclic carbene

被引：59

作者：

Kano, Taichi ^{[1
]}

Sasaki, Kouji ^{[1
]}

Konishi, Teppei ^{[1
]}

Mii, Haruka ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 27期

关键词：

cyanation; N-heterocyclic carbene; ANIONIC CHIRAL NUCLEOPHILES; STRECKER-TYPE REACTION; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; TRIMETHYLSILYL CYANIDE; IMIDAZOLE DERIVATIVES; BENZOIN CONDENSATION; ASYMMETRIC ADDITION; THIAZOLIUM; CYANOSILYLATION;

D O I：

10.1016/j.tetlet.2006.04.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthetic utility of N-heterocyclic carbenes was demonstrated by the trialkylsilylcyanation of aldehydes, ketones and imines. In the presence of a catalytic amount of 3a, the reactions with Me3SiCN proceeded smoothly to give the corresponding cyanohydrin trimethylsilyl ethers or amino nitrile derivatives in good to excellent yields. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4615 / 4618

页数：4

共 73 条

[1] Imidazolylidenes, imidazolinylidenes and imidazolidines [J].

Arduengo, AJ ;

Krafczyk, R ;

Schmutzler, R ;

Craig, HA ;

Goerlich, JR ;

Marshall, WJ ;

Unverzagt, M .

TETRAHEDRON, 1999, 55 (51) :14523-14534

[2]

Arend M, 1999, ANGEW CHEM INT EDIT, V38, P2873, DOI 10.1002/(SICI)1521-3773(19991004)38:19<2873::AID-ANIE2873>3.3.CO

[3]

2-G

[4] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726

[5] SYNTHETIC APPLICATIONS OF OPTICALLY-ACTIVE CYANOHYDRINS - ENANTIOSELECTIVE SYNTHESES OF THE HYDROXYAMIDES TEMBAMIDE AND AEGELINE, THE CARDIAC DRUG DENOPAMINE, AND SOME ANALOGS OF THE BRONCHODILATOR SALBUTAMOL [J].

BROWN, RFC ;

DONOHUE, AC ;

JACKSON, WR ;

MCCARTHY, TD .

TETRAHEDRON, 1994, 50 (48) :13739-13752

[6] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[7]

Choi MCK, 2002, HETEROCYCLES, V58, P645

[8] Catalytic generation of activated carboxylates:: Direct, stereoselective synthesis of β-hydroxyesters from epoxyaldehydes [J].

Chow, KYK ;

Bode, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8126-8127

[9] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

[10] Catalysis of benzoin condensation by conformationally-restricted chiral bicyclic thiazolium salts [J].

Dvorak, CA ;

Rawal, VH .

TETRAHEDRON LETTERS, 1998, 39 (19) :2925-2928

← 1 2 3 4 5 6 7 8 →