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Asymmetric Inverse-Electron-Demand Diels–Alder Reaction of β,γ-Unsaturated Amides through Dienolate Catalysis

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journal contribution
posted on 29.08.2019, 18:07 by Jialiang Qin, Yili Zhang, Cuiting Liu, Jun Zhou, Ruoting Zhan, Weiwen Chen, Huicai Huang
Reported herein is an inverse-electron-demand oxa-Diels–Alder reaction that is remotely β,γ-regioselective with β,γ-unsaturated amides and β,γ-unsaturated-α-ketoesters using a bifunctional catalyst. It can provide different kinds of dihydropyrans bearing three subsequent chiral carbon centers in good to high yield (61–99%) and with complete enantioselectivity (99 to >99% ee). Furthermore, a larger-scale experiment confirmed the reliability of the current reaction, and further effective transformation of the product has been realized.