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

doi:10.6023/cjoc201703013

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

NOTE

不对称高效构筑新颖螺环氧化吲哚α-甲基仲康酸酯

郭燕军, 孟晨红, 刘学立, 许丹倩, 夏爱宝

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 E-mail:xiaaibao@zjut.edu.cn
基金资助:
国家自然科学基金（No.21402176）资助项目.

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

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

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 E-mail:xiaaibao@zjut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No.21402176).

1. An Efficient Asymmetric Construction of Novel Spiro-Fused 2-Oxindoles/α-Methy-paraconic Ester.PDF(1420KB)

Abstract

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

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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]. Chin. J. Org. Chem., 2017, 37(10): 2776-2782.

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不对称高效构筑新颖螺环氧化吲哚α-甲基仲康酸酯

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

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