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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 10: 3382 - 3389

DOI: https://doi.org/10.6023/cjoc202208021

ARTICLES

Asymmetric Palladium-Catalyzed Aza-Wacker Reaction of Alkenes: Efficient Synthesis of Chiral 1,3-Oxazinan-2-ones

  • Xintuo Yang ,
  • Pinhong Chen ,
  • Guosheng Liu
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  • a State Key Laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032
    b Chang-Kung Chuang Institute, East China Normal University, Shanghai 200062
* Corresponding author. E-mail:

Received date: 2022-08-16

  Revised date: 2022-10-09

  Online published: 2022-10-12

Supported by

National Key R&D Program of China(2021YFA1500050); National Natural Science Foundation of China(21971255); National Natural Science Foundation of China(91956202); National Natural Science Foundation of China(21790330); National Natural Science Foundation of China(21821002); Science and Technology Commission of Shanghai Municipality(19590750400); Science and Technology Commission of Shanghai Municipality(21520780100); Science and Technology Commission of Shanghai Municipality(17JC1401200); Key Research Program of Frontier Sciences of Chinese Academy of Sciences(QYZDJSSW-SLH055); International Partnership Program of Chinese Academy of Sciences(121731KYSB20190016)

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Abstract

A Pd-catalyzed asymmetric aza-Wacker-type reaction with N-Ts carbamate as the nucleophile has been developed, which employed a C-6 substituted pyridinyl-oxazoline as the chiral ligand and benzoquinone (BQ) as the oxidant. This reaction provides an efficient access to chiral 1,3-oxazinan-2-ones with good efficiency and excellent enantioselectivity. Mechanistic studies indicated that the reaction is initiated by an intramolecular asymmetric aminopalladation.

Key words： aza-Wacker; palladium catalysis; asymmetric aminopalladation; chiral 1,3-oxazinan-2-ones; chiral pyridinyl- oxazoline

Cite this article

Xintuo Yang , Pinhong Chen , Guosheng Liu . Asymmetric Palladium-Catalyzed Aza-Wacker Reaction of Alkenes: Efficient Synthesis of Chiral 1,3-Oxazinan-2-ones[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3382 -3389 . DOI: 10.6023/cjoc202208021

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