Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (10): 2776-2782.DOI: 10.6023/cjoc201703013 Previous Articles     Next Articles



郭燕军, 孟晨红, 刘学立, 许丹倩, 夏爱宝   

  1. 浙江工业大学催化加氢研究中心 浙江省绿色农药清洁生产技术研究重点实验室 杭州 310014
  • 收稿日期:2017-03-06 修回日期:2017-05-24 发布日期:2017-06-02
  • 通讯作者: 夏爱宝
  • 基金资助:


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

Guo Yanjun, Meng Chenhong, Liu Xueli, Xu Danqian, Xia Aibao   

  1. Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Catalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014
  • Received:2017-03-06 Revised:2017-05-24 Published:2017-06-02
  • Contact: 10.6023/cjoc201703013
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21402176).

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.

Key words: asymmetric synthesis, spirooxindole γ-lactones, paraconic acids