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

The enantioselective reaction of a-substituted ig- 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 diastereoselectiv-ities. 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.

Automated summary

The enantioselective reaction of a-substituted ig-nitroacrylates with oxazol-5-(4H)-ones (oxazolones) to construct consecutive tetrasubstituted stereogenic centers was achieved. A cinchona alkaloid sulfonamide catalyst provided products with vicinal chiral centers that exhibited excellent enantio- and diastereoselectivities. The obtained products were further transformed into different chiral compounds without compromising their enantiopurity. Moreover, density functional theory (DFT) calculations were employed to elucidate the mechanism and origin of the observed stereoselectivity of the reaction.