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- Title
Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers.
- Authors
Zhi-Long Li; Rui Tan; Zhi-Ping Tong; Chao Liu; Yan-Kai Liu
- Abstract
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.
- Subjects
HEMIAMINALS; ORGANOCATALYSIS; ANNULATION
- Publication
Catalysts (2073-4344), 2016, Vol 6, Issue 5, p65
- ISSN
2073-4344
- Publication type
Article
- DOI
10.3390/catal6050065