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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 4, Issue -, Pages -Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.4.21
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Background Although the nucleophilic difluoromethylation of aldehydes, ketones, and imines has been realized with PhSO2CF2H and related reagents, there are still no reports on the enantioselective nucleophilic reactions. Results With a chiral quaternary ammonium salt as the catalyst and KOH as the base, we describe the first enantioselective difluoromethylation of aromatic aldehydes with PhSO2CF2H or Me3SiCF2SO2Ph. The enantioselectivity is substrate-dependent and for 2-chlorinated benzaldehyde an ee up to 64% was obtained. Conclusion These results provide some insights into the enantioselective nucleophilic difluoromethylation chemistry, which will stimulate further progress in this field.
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