期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 44, 页码 23641-23645出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202111376
关键词
asymmetric cycloaddition; gem-difluoromethylation; palladium; vinyl epoxide; vinylethylene carbonate
资金
- National Natural Science Foundation of China [21871282]
The asymmetric synthesis of 2,2-difluorinated tetrahydrofurans was achieved through palladium-catalyzed enantioselective formal [3+2] cycloaddition, resulting in enantioenriched products with up to 98% selectivity. The use of readily available (R)-BINAP ligand at a low loading enabled the production of a wide variety of difluorinated compounds in moderate to high yields, with the ability to obtain both chiral diastereomers in a single sequence.
The asymmetric synthesis of 2,2-difluorinated tetrahydrofurans was accomplished via enantioselective formal [3+2] cycloaddition catalyzed by palladium. The asymmetric reaction between gem-difluoroalkenes and racemic vinyl epoxides or vinylethylene carbonates resulted in the formation of enantioenriched 2,2-difluorotetrahydrofurans with an enantioselectivity up to 98 %. Notably, the reaction used the readily available (R)-BINAP as the ligand at a low loading and yielded a wide variety of difluorinated products in moderate to high yields. Both chiral diastereomers could be obtained in a single sequence.
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