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Tandem Double-Michael-Addition/Cyclization/Acyl Migration of 1,4-Dien-3-ones and Ethyl Isocyanoacetate: Stereoselective Synthesis of Pyrrolizidines

✍ Scribed by Jing Tan; Xianxiu Xu; Lingjuan Zhang; Yifei Li; Qun Liu


Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
611 KB
Volume
48
Category
Article
ISSN
0044-8249

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✦ Synopsis


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.magnified image


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