Enantioselective Construction of Consecutive Tetrasubstituted Stereogenic Centers by Reaction of α-Substituted β-Nitroacrylates with Oxazol-5-(4H)-ones Catalyzed by Cinchona Alkaloid Sulfonamide Catalysts.

The enantioselective reaction of α-substituted β-nitroacrylates with oxazol-5-(4H)-ones (oxazolones) to construct consecutive tetrasubstituted stereogenic centers was accomplished. A cinchona alkaloid sulfonamide catalyst afforded products bearing vicinal chiral centers with excellent enantio- and diastereoselectivities. The obtained products were successively converted into various chiral compounds without loss of their enantiopurity. Furthermore, density functional theory (DFT) calculations were performed to elucidate the mechanism and origin of the observed stereoselectivity of the reaction.

Citation

Kazuki Fujita, Momona Hattori, Tsunayoshi Takehara, Takeyuki Suzuki, Shuichi Nakamura. Enantioselective Construction of Consecutive Tetrasubstituted Stereogenic Centers by Reaction of α-Substituted β-Nitroacrylates with Oxazol-5-(4H)-ones Catalyzed by Cinchona Alkaloid Sulfonamide Catalysts. Organic letters. 2023 Apr 28;25(16):2835-2839

PMID: 37067189

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