Cy‐SaBOX/Copper(II)‐Catalyzed Highly Diastereo‐ and Enantioselective Synthesis of Bicyclic N,O Acetals

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  • Qiong‐Jie Liu
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 China
  • Lijia Wang
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 China
  • Qi‐Kai Kang
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 China
  • X. Peter Zhang
    Department of Chemistry, Merkert Chemistry Center Boston College Chestnut Hill MA 02467 USA
  • Yong Tang
    State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences 345 Lingling Lu Shanghai 200032 China

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Published
2016-06-28
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  • http://onlinelibrary.wiley.com/termsAndConditions#am
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DOI
  • 10.1002/anie.201603911
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Wiley

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<jats:title>Abstract</jats:title><jats:p>Facile and effective access for the asymmetric construction of the useful and important skeleton of the bicyclic N,O‐acetals is described. Cu<jats:sup>II</jats:sup>/SaBOX could catalyze the reaction of β,γ‐unsaturated α‐ketoesters with cyclic enamines efficiently, thus affording the desired products in excellent yields with excellent stereoselectivities (21 examples; up to 99 % yields; up to >95:5 d.r.; and 95–99 % <jats:italic>ee</jats:italic>). This reaction can be well performed on gram scale, even with only 1 mol % catalyst loading. The single‐crystal structures of the copper complexes lead to a good understanding of the stereo‐synergistic effects of the sidearm.</jats:p>

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