Citation: Hao Erjun, Zhang Qing, Zhang Qiying, Qu Guirong, Yang Xining, Guo Haiming. Efficient Synthesis of Spirocyclic Nucleosides via Michael Addition-Initiated Intermolecular Cyclopropanation Reaction[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3237-3243. doi: 10.6023/cjoc201904074 shu

Efficient Synthesis of Spirocyclic Nucleosides via Michael Addition-Initiated Intermolecular Cyclopropanation Reaction

Hao Erjun ^a ,
Zhang Qing ^a ,
Zhang Qiying ^a,, ,
Qu Guirong ^a ,
Yang Xining ^b ,
Guo Haiming ^a,,

a.
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
b.
Xinxiang Tuoxin Pharmaceutical Co., Ltd., Xinxiang, Henan 453000

Corresponding author: Zhang Qiying, zhangqiying@htu.edu.cn Guo Haiming, ghm@htu.edu.cn
Received Date: 30 April 2019
Revised Date: 7 June 2019
Available Online: 24 November 2019
Fund Project: the Henan Postdoctoral Science Foundation Funded Project 2015071Overseas Expertise Introduction Project for Discipline Innovation D17007Project supported by the National Natural Science Foundation of China (Nos. 21602045, U1604283), the Henan Postdoctoral Science Foundation Funded Project (No. 2015071) and Overseas Expertise Introduction Project for Discipline Innovation (111 Project, No. D17007)the National Natural Science Foundation of China 21602045Overseas Expertise Introduction Project for Discipline Innovation 111计划the National Natural Science Foundation of China U1604283

Figures(3)

An efficient route to synthesize 2'-spiro[2-oxocyclopentyl]cyclopropyl nucleoside analogues via KO^tBu promoted Michael addition-initiated cyclopropanation reactions of α-thymine acrylates with α-chloro-cycloalkanones has been developed. A wide range of C(2')-spirocyclic modified nucleoside analogues were obtained with excellent diastereoselectivities (>20:1) and good yields (up to 85%).
- spirocyclic nucleoside,
- cyclopropanation reaction,
- α-chloro-cycloalkanone
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沈阳化工大学材料科学与工程学院沈阳 110142