Journal
ORGANIC LETTERS
Volume 25, Issue 16, Pages 2835-2839Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c00783
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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.
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.
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