Citation: Guo Yanjun, Meng Chenhong, Liu Xueli, Xu Danqian, Xia Aibao. An Efficient Asymmetric Construction of Novel Spiro-Fused 2-Oxindoles/α-Methy-paraconic Ester[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2776-2782. doi: 10.6023/cjoc201703013 shu

An Efficient Asymmetric Construction of Novel Spiro-Fused 2-Oxindoles/α-Methy-paraconic Ester

Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Catalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Xia Aibao, xiaaibao@zjut.edu.cn
Received Date: 6 March 2017
Revised Date: 24 May 2017
Available Online: 2 October 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No.21402176)the National Natural Science Foundation of China 21402176

Figures(3)

Chiral spirooxindole γ-lactones with three stereogenic centres are rare. An efficient asymmetric construction of novel spiro-fused 2-oxindole/α-methy-paraconnic ester is reported, which was offered via organocatalytic Michael reaction of propaldehyde and olefinic oxindoles, with subsequent H₂O₂/K₂CO₃ system-mediated α-hydroxylation/hemiacetalization cascade reaction under oil/water two-phase conditions, and final oxidative γ-lactonization by pyridinium chlorochromate (PCC). The presented strategy features mild reaction conditions, excellent yields (91%~98%) and enatioselectiveties (87%~95%), and accordingly constitutes a facile and new method for the synthesis of chiral multisubstituted spirooxindole γ-lactones. All structures of new products were confirmed by ¹H NMR, ¹³C NMR and HRMS techniques.
- asymmetric synthesis,
- spirooxindole γ-lactones,
- paraconic acids
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