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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 11: 3237 - 3243

DOI: https://doi.org/10.6023/cjoc201904074

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

  • Erjun Hao ,
  • Qing Zhang ,
  • Qiying Zhang ,
  • Guirong Qu ,
  • Xining Yang ,
  • Haiming Guo
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  • aHenan 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

Received date: 2019-04-30

  Online published: 2019-06-24

Supported by

the National Natural Science Foundation of China(21602045);the National Natural Science Foundation of China(U1604283);the Henan Postdoctoral Science Foundation Funded Project(2015071);Overseas Expertise Introduction Project for Discipline Innovation(111计划);Overseas Expertise Introduction Project for Discipline Innovation(D17007)

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Abstract

An efficient route to synthesize 2'-spiro[2-oxocyclopentyl]cyclopropyl nucleoside analogues via KOtBu 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%).

Cite this article

Erjun Hao , Qing Zhang , Qiying Zhang , Guirong Qu , Xining Yang , Haiming Guo . 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

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