Cy‐SaBOX/Copper(II)‐Catalyzed Highly Diastereo‐ and Enantioselective Synthesis of Bicyclic N,O Acetals |
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| Authors: | Qiong‐Jie Liu Dr Lijia Wang Qi‐Kai Kang Prof?Dr X Peter Zhang Prof?Dr Yong Tang |
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| Institution: | 1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China;2. Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, USA;3. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China |
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| Abstract: | Facile and effective access for the asymmetric construction of the useful and important skeleton of the bicyclic N,O‐acetals is described. CuII/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 % ee). 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. |
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| Keywords: | asymmetric catalysis copper cycloaddition heterocycles X-ray diffraction |
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