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ABSTRACT: Background
Although the nucleophilic difluoromethylation of aldehydes, ketones, and imines has been realized with PhSO(2)CF(2)H 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 PhSO(2)CF(2)H or Me(3)SiCF(2)SO(2)Ph. 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.
SUBMITTER: Ni C
PROVIDER: S-EPMC2486490 | biostudies-literature | 2008
REPOSITORIES: biostudies-literature
Beilstein journal of organic chemistry 20080626
<h4>Background</h4>Although the nucleophilic difluoromethylation of aldehydes, ketones, and imines has been realized with PhSO(2)CF(2)H and related reagents, there are still no reports on the enantioselective nucleophilic reactions.<h4>Results</h4>With a chiral quaternary ammonium salt as the catalyst and KOH as the base, we describe the first enantioselective difluoromethylation of aromatic aldehydes with PhSO(2)CF(2)H or Me(3)SiCF(2)SO(2)Ph. The enantioselectivity is substrate-dependent and fo ...[more]