Ionic liquids as green solvents for the asymmetric synthesis of cyanohydrins catalysed by VO(salen) complexes

被引:71
作者
Baleizao, C
Gigante, B
Garcia, H
Corma, A
机构
[1] INETI, Dept Tecnol Ind Quim, P-1649038 Lisbon, Portugal
[2] CSIC, Inst Tecnol Quim, Valencia 46022, Spain
关键词
D O I
10.1039/b201497c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
It has been found that the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate is a good substitute solvent for CH2Cl2 to conduct the enantioselective cyanosilylation of aldehydes to their silylated cyanohydrins, using trimethylsilyl cyanide as reagent and a Schiff base vanadyl complex as catalyst. The mass balances ( > 90%), conversions ( > 80%) and enantiomeric excess (88% < ee < 90%) were high and comparable to those achieved in CH2Cl2. The ionic liquid containing the catalyst can be reused at least four times without loosing activity.
引用
收藏
页码:272 / 274
页数:3
相关论文
共 22 条
  • [1] How polar are room-temperature ionic liquids?
    Aki, SNVK
    Brennecke, JF
    Samanta, A
    [J]. CHEMICAL COMMUNICATIONS, 2001, (05) : 413 - 414
  • [2] BALEIZAO C, IN PRESSS
  • [3] Vanadium-catalyzed asymmetric cyanohydrin synthesis
    Belokon, YN
    North, M
    Parsons, T
    [J]. ORGANIC LETTERS, 2000, 2 (11) : 1617 - 1619
  • [4] Optimized catalysts for the asymmetric addition of trimethylsilyl cyanide to aldehydes and ketones
    Belokon, YN
    Green, B
    Ikonnikov, NS
    North, M
    Parsons, T
    Tararov, VI
    [J]. TETRAHEDRON, 2001, 57 (04) : 771 - 779
  • [5] Eyes on ionic liquids
    Freemantle, M
    [J]. CHEMICAL & ENGINEERING NEWS, 2000, 78 (20) : 37 - +
  • [6] FREEMANTLE M, 1992, ENCY CHEM TECHNOLOGY, P821
  • [7] Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications
    Gregory, RJH
    [J]. CHEMICAL REVIEWS, 1999, 99 (12) : 3649 - 3682
  • [8] Asymmetric synthesis of an (R)-cyanohydrin using enzymes entrapped in lens-shaped gels
    Gröger, H
    Capan, E
    Barthuber, A
    Vorlop, KD
    [J]. ORGANIC LETTERS, 2001, 3 (13) : 1969 - 1972
  • [9] Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation
    Huddleston, JG
    Visser, AE
    Reichert, WM
    Willauer, HD
    Broker, GA
    Rogers, RD
    [J]. GREEN CHEMISTRY, 2001, 3 (04) : 156 - 164
  • [10] Room temperature ionic liquids as novel media for 'clean' liquid-liquid extraction
    Huddleston, JG
    Willauer, HD
    Swatloski, RP
    Visser, AE
    Rogers, RD
    [J]. CHEMICAL COMMUNICATIONS, 1998, (16) : 1765 - 1766