DBU catalyzed cyanoacylation of ketones with acyl cyanides

被引：46
作者：
Zhang, W [1 ]
Shi, M [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 09期
关键词：
D O I：
10.1039/b602197b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of cyclohexanone with benzoyl cyanide catalyzed by amines provides the corresponding O-benzoyl cyanohydrin adducts in moderate to good yields under mild conditions. Among the catalysts, DBU was found to be the most effective promoter allowing the reaction to proceed smoothly at room temperature and to give the corresponding O-acyl cyanohydrin adducts in higher yields for a variety of substituted cyclohexanones, cyclopentanone, acetone or pentan-3-one and various acyl cyanides.
引用
收藏
页码：1671 / 1674
页数：4
相关论文
共 47 条
[1]   BENZOYL CYANIDE AS A SELECTIVE ACYLATING AGENT [J].
ABBAS, SA ;
HAINES, AH .
CARBOHYDRATE RESEARCH, 1975, 39 (02) :358-363
[2]  
Aloy J, 1913, CR HEBD ACAD SCI, V156, P1547
[3]   Solvent-free synthesis of cyanohydrin derivatives catalysed by triethylamine [J].
Baeza, A ;
Nájera, C ;
Retamosa, MD ;
Sansano, JM .
SYNTHESIS-STUTTGART, 2005, (16) :2787-2797
[4]   Asymmetric synthesis of O-benzoyl cyanohydrins by reaction of aldehydes with benzoyl cyanide catalysed by BINOLAM-Ti(IV) complexes [J].
Baeza, A ;
Nájera, C ;
Sansano, JM ;
Saá, JM .
TETRAHEDRON-ASYMMETRY, 2005, 16 (14) :2385-2389
[5]   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
[6]   Catalytic, asymmetric synthesis of cyanohydrin ethyl carbonates [J].
Belokon, YN ;
Blacker, AJ ;
Clutterbuck, LA ;
North, M .
ORGANIC LETTERS, 2003, 5 (23) :4505-4507
[7]  
Belokon YN, 2002, HELV CHIM ACTA, V85, P3301, DOI 10.1002/1522-2675(200210)85:10<3301::AID-HLCA3301>3.0.CO
[8]  
2-2
[9]   Catalytic asymmetric synthesis of O-acetyl cyanohydrins from KCN, Ac2O and aldehydes [J].
Belokon, YN ;
Gutnov, AV ;
Moskalenko, MA ;
Yashkina, LV ;
Lesovoy, DE ;
Ikonnikov, NS ;
Larichev, VS ;
North, M .
CHEMICAL COMMUNICATIONS, 2002, (03) :244-245
[10]  
Brunel J.- M., 2004, ANGEW CHEM, V116, P2810
12345