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

Tan Jing | Zendy; Xu Xianxiu | Zendy; Zhang Lingjuan | Zendy; Li Yifei | Zendy; Liu Qun | Zendy

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

Author(s) -

Tan Jing,

Xu Xianxiu,

Zhang Lingjuan,

Li Yifei,

Liu Qun

Publication year - 2009

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200805703

Subject(s) - stereocenter , pyrrolizidine , michael reaction , stereoselectivity , chemistry , tandem , stereochemistry , catalysis , organic chemistry , enantioselective synthesis , materials science , composite material

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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