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  • Lipase-Catalyzed Kinetic Resolution of Cyclic trans-1,2-DiolsBearing a Diester Moiety: Synthetic Application to ChiralSeven-Membered-Ring α,α-Disubstituted α-Amino Acid
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  • Chiral cycloalkane-trans-1,2-diols (±)-3 and (±)-8 having a diester moiety have been prepared fromdimethyl dialkenylmalonate using olefin metathesis by Grubbs catalyst, followed by epoxidation andacidic hydrolysis. Kinetic resolution of racemic cyclopentane-trans-1,2-diol (±)-3 by lipase-catalyzedtransesterification afforded an optically active monoacetate (−)-5 of 95% ee in 46% yield and the recovereddiol (−)-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 enantiomerselectivity of racemic cyclic trans-1,2-diols bearing a diester moiety by lipases (Amano PS and AmanoAK) was opposite to that of the reported simple racemic cycloalkane-trans-1,2-diols. To explain thelipase-catalyzed enantiomer selectivity, computer modeling of lipase−substrate complexes was performed.Furthermore, the optically active diester (−)-8 could be efficiently converted into an optically activeseven-membered-ring α,α-disubstituted amino acid (4R,5R)-(−)-15.
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