A two-step sequential biocatalytic process for the synthesis of chiral hydroxyesters that combines a lipase-catalyzed decarboxylative aldol reaction followed by kinetic resolution has been developed. The excellent combination of conventional and unconventional functions provides an attractive route for expanding the applications of biocatalysis.
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Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives.
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Bioprocess Engineering Department, Institute of Industrial and Environmental Biotechnology, National Institute of Genetic Engineering and Biotechnology (NIGEB), Tehran, Iran.
The Candida antarctica lipase B (Novozym 435) is found to catalyze a novel decarboxylative Michael addition in vinylogous carbamate systems for the synthesis of 1,4-benzoxazinone derivatives. The reaction goes through Michael addition, ester hydrolysis and decarboxylation. A possible mechanism is suggested, with simultaneous lipase-catalyzed Michael addition and ester hydrolysis.
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Department of Chemistry, Zhejiang University, Hangzhou 310027, P.R. China.
A double-enzyme-catalyzed strategy for the synthesis of enantiocomplementary vicinal fluoro alcohols through a one-pot, three-step process including lipase-catalyzed hydrolysis, spontaneous decarboxylative fluorination, and subsequent ketoreductase-catalyzed reduction was developed. With this approach, β-ketonic esters were converted to the corresponding vicinal fluoro alcohols with high isolated yields (up to 92%) and stereoselectivities (up to 99%). This new cascade process addresses some issues in comparison with traditional methods such as environmentally hazardous reaction conditions and low stereoselectivity outcome.
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Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan.
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View Article and Find Full Text PDFBiocatalytic synthesis of optically active hydroxyesters via lipase-catalyzed decarboxylative aldol reaction and kinetic resolution.
Appl Biochem Biotechnol
May 2014
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, People's Republic of China.
A two-step sequential biocatalytic process for the synthesis of chiral hydroxyesters that combines a lipase-catalyzed decarboxylative aldol reaction followed by kinetic resolution has been developed. The excellent combination of conventional and unconventional functions provides an attractive route for expanding the applications of biocatalysis.
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