Double Enzyme-Catalyzed One-Pot Synthesis of Enantiocomplementary Vicinal Fluoro Alcohols
Jiajie Fan, Yongzhen Peng, Weihua Xu, Anlin Wang, Jian Xu, Hui‐Lei Yu, Xianfu Lin, Qi Wu
Abstract
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.
Topics & Concepts
VicinalChemistryStereoselectivityCatalysisHydrolysisOrganic chemistryLipaseCascade reactionCascadeEnzymeCombinatorial chemistryChromatographyFluorine in Organic ChemistryCarbohydrate Chemistry and SynthesisCyclopropane Reaction Mechanisms