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Asymmetric Catalysis Using Modularly Designed Organocatalysts: Synthesis of Fused Tricyclic Pyrano‐Pyrano[2,3‐c]pyrrol Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2019-05-02 , DOI: 10.1002/adsc.201900254
Xue Lu 1 , Yili Zhang 1 , Yichen Wang 1 , Yuzhen Chen 1 , Weiwen Chen 1 , Ruoting Zhan 1 , John C.‐G. Zhao 2 , Huicai Huang 1
Affiliation  

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‐pyrano[3′,2′:5,6]pyrano[2,3‐c]pyrrol derivatives in high yields (up to 99%) with good to excellent enantioselectivities (up to 99% ee) under mild reaction conditions.

中文翻译:

模块化设计的有机催化剂的不对称催化:熔融三环吡喃-吡喃并[2,3-c]吡咯衍生物的合成

已发现涉及醛和二氧杂吡咯烷的高度对映选择性的有机催化迈克尔加成缩醛/ oxa-Michael反应。不对称反应是由金鸡纳生物碱衍生物和氨基酸自组装而成的模块化设计的有机催化剂(MDO)介导的,提供一系列光学活性的三环六氢-2 H-吡喃[3',2':5,6]吡喃[2,在温和的反应条件下,3- c ]吡咯衍生物的收率高(高达99%),对映选择性很好(至ee高达99%)。
更新日期:2019-05-02
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