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| Intramolecular (4+3) cycloadditions of nitrogen-tethered epoxy enosilanes for the synthesis of heteropolycycles |
| Jiayun Hea, Shuk Mei Lama, Jerome P. L. Nga, Wing-Tak Wongb, Pauline Chiua |
a State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Hong Kong, China;
b Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, China |
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| Guide Furans bearing epoxy enolsilane units linked by a nitrogen heteroatom tether undergo intramolecular (4 + 3) cycloadditions to generate bis-heteroatomic polycyclic adducts having piperidine moieties in their frameworks. The cycloadducts, ultimately derived from furfural, a renewal chemical feedstock, are obtained with up to 4:1 dr and with ee retained from the epoxide. |
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Abstract Furans bearing epoxy enolsilane units via a tether that incorporates a nitrogen heteroatom, undergo intramolecular (4 + 3) cycloadditions to generate bis-heteroatomic polycyclic adducts having piperidine moieties in their frameworks. The cycloadducts, ultimately derived from furfural, a renewal chemical feedstock, are obtained with up to 4:1 dr and with ee retained from the epoxide.
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Received: 27 February 2019
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| Fund:This work was supported by the Research Grants Council General Research Fund (No. 17301314); the State Key Laboratory of Synthetic Chemistry; and the University of Hong Kong. We thank the University of Hong Kong for a University Postgraduate Fellowship to JH, a Hung Hing Ying Postgraduate Scholarship to JPLN, and exploratory work by Dr. Kong Ching Wong. |
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Corresponding Authors:
Pauline Chiu
E-mail: pchiu@hku.hk
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