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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 11: 4320 - 4326

DOI: https://doi.org/10.6023/cjoc202106040

ARTICLES

Samarium Diiodide Promoted the Addition-Ring-Opening Reaction of 2-Piperidinone with α,β-Unsaturated Esters

  • Jian-Ting Sun ,
  • Ling-Yan Chen ,
  • Bang-Guo Wei
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  • a College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620
    b School of Pharmacy, Fudan University, Shanghai 201203
* Corresponding author. E-mail:

Received date: 2021-06-22

  Revised date: 2021-07-20

  Online published: 2021-08-25

Supported by

Postgraduate Students Innovation Program(20KY0431)

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Abstract

A convenient approach to N-Boc amino ketones 3a~3l has been developed, which features a SmI2 prompted one-pot radical addition-ring opening process of 2-piperidinone with α,β-unsaturated esters. Moreover, the indolizidine skeleton (6) has been successfully synthesized from the key methyl (S)-8-((tert-butoxycarbonyl)amino)-5-((tert-butyl- dimethylsilyl)oxy)-4-oxooctanoate (3e), which undergoes one-pot deprotection-condensation-reduction-amination process.

Key words： samarium diiodide; 2-piperidinone; radical addition-ring opening; indolizidine

Cite this article

Jian-Ting Sun , Ling-Yan Chen , Bang-Guo Wei . Samarium Diiodide Promoted the Addition-Ring-Opening Reaction of 2-Piperidinone with α,β-Unsaturated Esters[J]. Chinese Journal of Organic Chemistry, 2021 , 41(11) : 4320 -4326 . DOI: 10.6023/cjoc202106040

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CCDC 2090177 (5) contains the supplementary crystallographic data for this paper. These data are free of charge from The Cambridge Crystallographic Centre via www.ccdc.cam.ac.uk/datarequest/cif.
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