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Tandem Double‐Michael‐Addition/Cyclization/Acyl Migration of 1,4‐Dien‐3‐ones and Ethyl Isocyanoacetate: Stereoselective Synthesis of Pyrrolizidines
Authors:Jing Tan  Xianxiu Xu Dr.  Lingjuan Zhang  Yifei Li  Qun Liu Prof.
Affiliation:Department of Chemistry, Northeast Normal University, Changchun, 130024 (PR China), Fax: (+86)?431‐8509‐9759
Abstract:Up to four adjacent stereocenters can be formed stereoselectively in the construction of a pyrrolizidine unit through a novel organocatalytic reaction that involves treatment of various dienones with ethyl isocyanoacetate (see scheme; DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene). Mechanisms for this atom‐economic, one‐pot synthesis have been proposed.
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Keywords:domino reactions  Michael addition  pyrrolizidines  synthetic methods
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