Efficient Lipase-catalyzed Enantioselective Acylation under Reduced Pressure Conditions in an Ionic Liquid Solvent System

Itoh, Toshiyuki; Akasaki, Eri; Nishimura, Yoshihito

doi:10.1246/cl.2002.154

Cited by 83 publications

(36 citation statements)

References 13 publications

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“…65 Hence, the effects of ionic liquid reaction media on the resolution of the arylalkanols 20-31 (see Scheme 2) in the presence of, mainly, CaLB and PcL have been investigated. 33,107,108,113,205,206 Vinyl acetate was almost universally adopted as the acyl donor.…”

Section: Lipases and Esterasesmentioning

confidence: 99%

“…113 A loss of activity was observed, which was ascribed to the accumulation of inhibiting acetaldehyde oligomers in the ionic liquid phase. 205 In [BMMIm][BF4], polymer formation did not take place, presumably because the slightly acidic position at C-2 in the imidazolium ring is blocked. 111 The ionic liquid phase containing the biocatalyst could now be recycled five times without significant activity loss.…”

Section: Catalyst Recyclingmentioning

confidence: 99%

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Biocatalysis in Ionic Liquids

2007

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Fred van Rantwijk (1943) studied organic chemistry at the Delft University of Technology, where he remained as a staff member. He received his Ph.D. in 1980, for work under the guidance of Professor H. van Bekkum. Since the late 1980s he has been working on the application of enzymes in organic synthesis. His particular research interests are the use of enzymes in nonnatural reactions and nonnatural media, enzyme immobilization, and transformations using multi-enzyme systems.Roger Sheldon (1942) received a Ph.D. in organic chemistry from the University of Leicester (U.K.) in 1967. This was followed by postdoctoral studies with Prof. Jay Kochi in the U.S. From 1969 to 1980 he was with Shell Research in Amsterdam, and from 1980 to 1990 he was R&D Director of DSM Andeno. In 1991 he moved to his present position as Professor of biocatalysis and organic chemistry at the Delft University of Technology (The Netherlands). His primary research interests are in the application of catalytic methodologiesshomogeneous, heterogeneous, and enzymaticsto organic synthesis, particularly in relation to fine chemicals production. He developed the concepts of E factors and atom utilization for assessing the environmental impact of chemical processes.

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Section: Lipases and Esterasesmentioning

confidence: 99%

Section: Catalyst Recyclingmentioning

confidence: 99%

Biocatalysis in Ionic Liquids

2007

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“…The separation of products from enzyme-ILs phase can be facilitated by the inherently low vapour pressure of ILs allowing for easy removal of volatile substances. Thus, products isolation can be carried out by sublimation or distillation [47]. However, such methods are too energetically intensive for application on larger scale.…”

Section: Fig (5)mentioning

confidence: 99%

(Bio)Catalytic Continuous Flow Processes in scCO2 and/or ILs: Towards Sustainable (Bio)Catalytic Synthetic Platforms

Lozano¹,

García‐Verdugo²,

Luis³

et al. 2011

COS

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This review highlights the tool box for the development of continuous green/sustainable processes aimed at the synthesis of fine chemicals. By combining either chemical and/or biological catalysts with biphasic systems based on neoteric solvents, e.g. ionic liquids (ILs) and supercritical carbon dioxide (scCO2), interesting alternatives to organic solvents for designing continuous clean (bio)transformations methods are growing that directly provide pure products. The classical advantages of scCO2 -its ability to extract, dissolve and transport chemicals-are complemented by the high catalytic efficiency of enzymes in ILs. Enzyme behavior in scCO2 and ILs, as well as the phase behavior of ILs/scCO2, are key parameters for carrying out integral green bioprocesses in continuous operation. The preparation, main characteristics and advantages of monolithic microreactors and miniflow reactors for the synthesis of fine chemicals by continuous flow (bio)catalytic processes are underlined. Examples where the use of continuous flow techniques for multi-step synthesis enables multiple reaction steps to be combined into a single continuous operation are provided.

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“…Itoh et al [77] have demonstrated the kinetic resolution of some allylic alcohols in ionic liquid media under reduced pressure. An efficient enzymatic pathway has been developed for the synthesis of enantiopure allylic alcohols from corresponding ␣,␤-unsaturated ketones in this laboratory by employing onepot reduction followed by lipase-mediated resolution protocol in high enantiopurity (Scheme 17) [78].…”

Section: Resolution Of Allylic Alcoholsmentioning

confidence: 99%