Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles |
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| Authors: | Naveen Kumar Akshay Kumar Subash Chandra Sahoo Swapandeep Singh Chimni |
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| Affiliation: | 1. Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry-II, Guru Nanak Dev University, Amritsar, India;2. Department of Chemistry, DAV University, Jalandhar, Punjab, India;3. Department of Chemistry and Center of Advanced Studies in Chemistry-II, Panjab University, Chandigarh, India |
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| Abstract: | Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules. |
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| Keywords: | 3,3-disubstituted oxindoles Candida antarctica lipase enantioselective kinetic resolution quaternary stereocenter |
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