Enantioselective Reaction of 2H-Azirines with Oxazol-5-(4H)-ones Catalyzed by Cinchona Alkaloid Sulfonamide Catalysts.

The enantioselective reaction of 2H-azirines with oxazol-5-(4H)-ones (oxazolones) using a cinchona alkaloid sulfonamide catalyst has been developed. The reaction proceeded at the C-2 position of oxazolones to afford products with consecutive tetrasubstituted stereogenic centers in high yield with high diastereo- and enantioselectivity. The obtained aziridines were converted into various chiral compounds without loss of enantiopurity.

Citation

Kazuki Fujita, Masataka Miura, Yasuhiro Funahashi, Tsubasa Hatanaka, Shuichi Nakamura. Enantioselective Reaction of 2H-Azirines with Oxazol-5-(4H)-ones Catalyzed by Cinchona Alkaloid Sulfonamide Catalysts. Organic letters. 2021 Mar 19;23(6):2104-2108

PMID: 33650878

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