One-Pot Enantioselective Synthesis of 2‑Pyrrolidinone Derivatives Bearing a Trifluoromethylated All-Carbon Quaternary Stereocenter

A new methodology for the one-pot enantioselective construction of 2-pyrrolidinone derivatives bearing a trifluoromethylated all-carbon quaternary stereocenter at the 4-position has been described. This strategy combines an organocatalytic conjugate addition of nitroalkanes to isatin-derived α-trifl...

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Veröffentlicht in:Organic letters 2019-12, Vol.21 (23), p.9584-9588
Hauptverfasser: Jia, Zhuqing, Hu, Xiaoyi, Zhao, Yunlong, Qiu, Fayang G, Chan, Albert S. C, Zhao, Junling
Format: Artikel
Sprache:eng
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Zusammenfassung:A new methodology for the one-pot enantioselective construction of 2-pyrrolidinone derivatives bearing a trifluoromethylated all-carbon quaternary stereocenter at the 4-position has been described. This strategy combines an organocatalytic conjugate addition of nitroalkanes to isatin-derived α-trifluoromethyl acrylates and a reduction/lactamization process, affording the corresponding products in moderate to high yields (50–95%) with generally excellent stereoselectivities (up to 96% ee and >20:1 dr).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03758