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Diastereoselective and Enantioselective Synthesis of Multi-Functionalized Isoxazoline-N-Oxides through Asymmetric [4+1] Annulations |
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| Authors: | Dr Mengzhou Wang Jing Wang Dr Wen Shen Xuan-sheng Xie Dr Liang Qi Prof Dr Jian-wu Xie |
| Institution: | 1. School of Biological and Pharmaceutical Sciences, Shaanxi University of Science & Technology, 710021 Xi'an, P. R. China
These authors contributed euqally to this work.;2. Department of Chemistry and Life Science, Zhejiang Normal University, 321004 Jinhua, P. R. China These authors contributed euqally to this work.;3. School of Biological and Pharmaceutical Sciences, Shaanxi University of Science & Technology, 710021 Xi'an, P. R. China |
| Abstract: | A diastereoselective and enantioselective formal 4+1] ylide annulation of chiral sulfonium salts with various substituted Morita-Baylis-Hillman (MBH) adducts leading to optically active isoxazoline N-oxides with three chiral carbon centers has been explored. The salient features of this methodology include a high diastereo- and enantioselective transformation, easily accessible starting materials, and mild reaction conditions. In addition, the isoxazoline N-oxides products can be conveniently transformed into functionalized compounds. |
| Keywords: | annulation diastereoselective enantioselective isoxazoline N-oxide Morita-Baylis-Hillman |