Asymmetric Catalysis Using Modularly Designed Organocatalysts: Synthesis of Fused Tricyclic Pyrano‐Pyrano[2,3‐c]pyrrol Derivatives

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Asymmetric Catalysis Using Modularly Designed Organocatalysts: Synthesis of Fused Tricyclic Pyrano‐Pyrano[2,3‐c]pyrrol Derivatives

Lu, Xue; Zhang, Yili; Wang, Yichen; Chen, Yuzhen; Chen, Weiwen; Zhan, Ruoting; Zhao, John C.‐G.; Huang, Huicai

Advanced synthesis & catalysis, July 2, 2019, Volume: 361, Issue: 13

Journal Article

A highly enantioselective organocatalytic Michael addition‐acetalation/oxa‐Michael reaction involving aldehydes and dioxopyrrolidines has been discovered. The asymmetric reaction is mediated by modularly designed organocatalysts (MDOs) self‐assembled from cinchona alkaloid derivatives and amino acids providing a range of optically active tricyclic hexahydro‐2H‐pyrano3′,2′:5,6pyrano2,3‐cpyrrol derivatives in high yields (up to 99%) with good to excellent enantioselectivities (up to 99% ee) under mild reaction conditions.

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