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PPL在催化合成中的应用


Highly Efficient Synthesis of Enantiomerically Enriched 2-Hydroxymethylaziridines by Enzymatic Desymmetrization

Org. Lett.20079 (2), pp 215–218


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Both enantiomers of protected and unprotected 2-hydroxymethylaziridines are efficiently and enantiospecifically synthesized by using a combination of enzymatic and synthetic methods. PPL was used for lipase-catalyzed desymmetrization of N-protected serinol.


Enantioselective Enzymatic Desymmetrization of Prochiral Allenic Diols

Angew. Chem. Int. Ed. 2011, 50(41), 9731


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Crude lipase from porcine pancreas acts as a highly efficient biocatalyst in the enantioselective transesterification of prochiral allendiols. Following a simple synthetic protocol, highly functionalized axially chiral allenes are obtained in high yields and excellent enantiopurity (see scheme).


One-Pot Synthesis of Spirooxindole Derivatives Catalyzed by Lipase in the Presence of Water

Adv. Synth. Catal.  2011, 353, 371


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A facile one-pot synthesis route to spirooxindole derivatives was developed by combining the three types of catalytic activities of lipase from porcine pancreas (PPL) in the presence of water, i.e., the Knoevengel condensation, Michael addition and cyclization. PPL showed excellent catalytic activity and have a good adaptability to different substrates in the reaction. All the reactions go smoothly and provide spirooxindole derivatives with high yield under the mild conditions. This lipase-catalyzed multistep conversion method has provided a new strategy to synthesize spirooxindole derivatives and expanded the application of biocatalysts.


Lipase-Catalyzed Stereoselective Cross-Aldol Reaction Promoted by Water

DOI: 10.1002/cctc.201200890


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PPL, lipase from porcine pancreas, is first reported to catalyze direct asymmetric aldol reactions between aromatic aldehydes and cyclic ketones. More importantly, the catalytic activity of PPL was greatly promoted by a small quantity of water at 37 °C. A wide range of aromatic aldehydes reacted with cyclic ketones to provide the corresponding aldol products with high yields (up to 99 %) and moderate to good stereoselectivity (up to 90 % ee and 99:1 dr).

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