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Highly Efficient Route for Enantioselective Preparation of Chlorohydrins via Dynamic Kinetic Resolution
Org. Lett.200810 (21), pp 4807–4810


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     Dynamic kinetic resolution (DKR) of various aromatic chlorohydrins with the use ofPseudomonas cepacia lipase (PS-C “Amano” II) and ruthenium catalyst 1 afforded chlorohydrin acetates in high yields and high enantiomeric excesses. These optically pure chlorohydrin acetates are useful synthetic intermediates and can be transformed to a range of important chiral compounds.


Robust Enzymatic Resolution of 3-Fluoromandelic Acid with Lipase PS Supported on Celite

Org. Process Res. Dev.201216 (7), pp 1312–1316



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   The resolution of different mandelic acids using the lipase PS Amano” SD enzyme is described. By supporting the lyophilized enzyme over Celite, both the activity and the stability of lipase PS in organic media were significantly improved, enabling the robust resolution scale-up of 3-fluoromandelic acid. The methodology was extended to produce a range of optically pure (R)-mandelic acids, avoiding tedious extractions or chromatography.


Lipase-Catalyzed Kinetic Resolution of Cyclic trans-1,2-Diols Bearing a Diester Moiety: Synthetic Application to Chiral Seven-Membered-Ring α,α-Disubstituted α-Amino Acid

J. Org. Chem.200772 (20), pp 7750–7756



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    Chiral cycloalkane-trans-1,2-diols (±)-3 and (±)-8 having a diester moiety have been prepared from dimethyl dialkenylmalonate using olefin metathesis by Grubbs catalyst, followed by epoxidation and acidic hydrolysis. Kinetic resolution of racemic cyclopentane-trans-1,2-diol (±)-3 by lipase-catalyzed transesterification afforded an optically active monoacetate (-)-5 of 95% ee in 46% yield and the recovered diol (-)-3 of 92% ee in 51% yield, and that of cycloheptane-trans-1,2-diol (±)-8 gave a monoacetate (+)-10 of 95% ee in 51% yield and the diol (-)-8 of >99% ee in 43% yield, respectively. The enantiomer selectivity of racemic cyclictrans-1,2-diols bearing a diester moiety by lipases (Amano PS and Amano AK) was opposite to that of the reported simple racemic cycloalkane-trans-1,2-diols. To explain the lipase-catalyzed enantiomer selectivity, computer modeling of lipase-substrate complexes was performed. Furthermore, the optically active diester (-)-8 could be efficiently converted into an optically active seven-membered-ring α,α-disubstituted amino acid (4R,5R)-(-)-15.



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