Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers

نویسندگان

  • Zhi-Long Li
  • Chao Liu
  • Rui Tan
  • Zhi-Ping Tong
  • Yan-Kai Liu
  • Aurelio G. Csákÿ
چکیده

Lactols and cyclic hemiaminals were directly used in a one-pot organo/organo dual catalytic system induced [2+2+2] tandem reaction for the asymmetric construction of six-membered carbocycles. The enamine-based stereoselective Michael addition of lactols or cyclic hemiaminals to electron-deficient olefinic oxindole motifs provided chiral C4 components, which were further combined with triethylamine catalyzed Michael/Henry sequential reactions affording spirocyclic oxindole derivatives containing six continuous stereogenic centers with excellent enantioselectivities as a single diastereoisomer. All these desired products have versatile molecular complexity, which might have potential applications in synthetic organic chemistry and the pharmaceutical industry.

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تاریخ انتشار 2016