Stereoselective Synthesis of Fluoroalkanes via FLP Mediated Monoselective C─F Activation of Geminal Difluoroalkanes
Source abstract
Abstract
Abstract A method of desymmetrization of geminal difluoroalkanes using frustrated Lewis pair (FLP) mediated monoselective C–F activation where a chiral sulfide is the Lewis base component is reported. The stereoselective reaction provides generally high yields of diastereomeric sulfonium salts with dr of up to 95:5. The distribution of diastereomers is found to be thermodynamically controlled via facile sulfide exchange. The use of enantiopure chiral sulfides allows for high stereospecificity in nucleophilic substitution reactions and the formation of stereoenriched products.
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Research context
OpenAlex topics: Fluorine in Organic Chemistry · Asymmetric Synthesis and Catalysis · Inorganic Fluorides and Related Compounds
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Chemistry National University of Singapore Singapore 117543 Singapore
Research Centre for Natural Sciences Institute of Organic Chemistry Budapest 1117 Hungary
School of Chemistry and Molecular Biosciences The University of Queensland St Lucia 4067 Australia
Funding
Agency for Science, Technology and Research · Australian Research Council
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