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Open AccessCommunication
Catalysts 2016, 6(5), 65; doi:10.3390/catal6050065

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

1
School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China
2
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Aurelio G. Csákÿ
Received: 17 March 2016 / Revised: 13 April 2016 / Accepted: 15 April 2016 / Published: 27 April 2016
(This article belongs to the Special Issue Metal-free Organocatalysis)
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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. View Full-Text
Keywords: asymmetric organocatalysis; tandem reaction; lactol; cyclic hemiaminal; [2+2+2] annulation; spirocyclic oxindole asymmetric organocatalysis; tandem reaction; lactol; cyclic hemiaminal; [2+2+2] annulation; spirocyclic oxindole
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Li, Z.-L.; Liu, C.; Tan, R.; Tong, Z.-P.; Liu, Y.-K. Organocatalytic, Asymmetric [2+2+2] Annulation to Construct Six-Membered Spirocyclic Oxindoles with Six Continuous Stereogenic Centers. Catalysts 2016, 6, 65.

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