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 d...

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Bibliographic Details
Published in:Organic letters 2023-04, Vol.25 (16), p.2835-2839
Main Authors: Fujita, Kazuki, Hattori, Momona, Takehara, Tsunayoshi, Suzuki, Takeyuki, Nakamura, Shuichi
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00783