Enantioselective nucleophilic difluoromethylation of aromatic aldehydes with Me3SiCF2SO2Ph and PhSO2CF2H reagents catalyzed by chiral quaternary ammonium salts
Background<p>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.</p><p>Results</p><p>With a chiral quaternary am...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2008-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Online Access: | https://doi.org/10.3762/bjoc.4.21 |
| Summary: | Background<p>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.</p><p>Results</p><p>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.</p><p>Conclusion</p><p>These results provide some insights into the enantioselective nucleophilic difluoromethylation chemistry, which will stimulate further progress in this field.</p> |
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| ISSN: | 1860-5397 |