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Molecules 2017, 22(7), 1096; doi:10.3390/molecules22071096

Enantioselective Michael Addition of Cyclic β-Diones to α,β-Unsaturated Enones Catalyzed by Quinine-Based Organocatalysts

College of Chemistry and Environment Protection Engineering, Southwest Minzu University, Chengdu 610041, China
Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University, Chengdu 610031, China
Author to whom correspondence should be addressed.
Received: 16 May 2017 / Revised: 25 June 2017 / Accepted: 26 June 2017 / Published: 30 June 2017
(This article belongs to the Special Issue Asymmetric Synthesis 2017)
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An enantioselective (52–98% ee) Michael addition between cyclic β-diones and α,β-unsaturated enones was established in the presence of quinine-based primary amine or squaramide. A variety of cinnamones were smoothly converted into the desired 3,4-dihydropyrans in moderate to high yields (63–99%). Chalcones were also suitable acceptors and gave rise to the expected adducts in satisfactory yields (31–99%). The resulting adducts readily underwent further modification to form fused 4H-pyran or 2,3-dihydrofuran. View Full-Text
Keywords: cyclic β-dione; cinnamone; chalcone; michael addition; enantioselective cyclic β-dione; cinnamone; chalcone; michael addition; enantioselective

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Wang, Q.; Wang, W.; Ye, L.; Yang, X.; Li, X.; Zhao, Z.; Li, X. Enantioselective Michael Addition of Cyclic β-Diones to α,β-Unsaturated Enones Catalyzed by Quinine-Based Organocatalysts. Molecules 2017, 22, 1096.

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