N‐Heterocyclic Carbene Catalyzed Enantioselective α‐Fluorination of Aliphatic Aldehydes and α‐Chloro Aldehydes: Synthesis of α‐Fluoro Esters,Amides, and Thioesters |
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| Authors: | Dr Xiuqin Dong Dr Wen Yang Dr Weimin Hu Prof?Dr Jianwei Sun |
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| Affiliation: | 1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China);2. Department of Chemistry, Jinan University, Guangzhou 510632 (China) |
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| Abstract: | The asymmetric fluorination of azolium enolates that are generated from readily available simple aliphatic aldehydes or α‐chloro aldehydes and N‐heterocyclic carbenes (NHCs) is described. The process significantly expands the synthetic utility of NHC‐catalyzed fluorination and provides facile access to a wide range of α‐fluoro esters, amides, and thioesters with excellent enantioselectivity. Pyrazole was identified as an excellent acyl transfer reagent for catalytic amide formation. |
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| Keywords: | asymmetric catalysis enolates fluorine N‐heterocyclic carbenes organocatalysis |
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