4.7 Article

One-Pot Asymmetric Synthesis of Spiropyrazolone-Linked Cyclopropanes and Benzofurans through a General Michael Addition/Chlorination/Nucleophilic Substitution Sequence

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 16, Pages 10292-10305

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01454

Keywords

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Funding

  1. NSFC [21632003, 21871116, 21572087]
  2. key program of Gansu province [17ZD2GC011]
  3. 111 program from the MOE of P. R. China

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A sequential and general strategy has been successfully developed for the synthesis of spiropyrazolone scaffolds. This intriguing transformation of the asymmetric multicomponent catalysis process was realized with the combination of Michael addition/chlorination/nucleophilic substitution in a one-pot sequence, giving rise to a series of spiropyrazolones with fully substituted cyclopropanes and spiro-dihydrobenzofurans containing continuous stereogenic centers in good yields with excellent stereoselectivities.

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