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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.