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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Published in:Organic letters 2023-04, Vol.25 (16), p.2835-2839
Main Authors: Fujita, Kazuki, Hattori, Momona, Takehara, Tsunayoshi, Suzuki, Takeyuki, Nakamura, Shuichi
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Language:English
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cited_by cdi_FETCH-LOGICAL-a1909-1e143f5f01081aca839292abb0aa1b7872d45fca9e51a3c3b13b7bd7ba67bc0a3
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container_title Organic letters
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creator Fujita, Kazuki
Hattori, Momona
Takehara, Tsunayoshi
Suzuki, Takeyuki
Nakamura, Shuichi
description 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.
doi_str_mv 10.1021/acs.orglett.3c00783
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title 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
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