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Reactions of Iminium Ions with Michael Acceptors through a Morita–Baylis–Hillman‐Type Reaction: Enantiocontrol and Applications in Synthesis
Author(s) -
Myers Eddie L.,
de Vries Johannes G.,
Aggarwal Varinder K.
Publication year - 2007
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.200604715
Subject(s) - iminium , electrophile , chemistry , trifluoromethanesulfonate , adduct , type (biology) , michael reaction , baylis–hillman reaction , organocatalysis , medicinal chemistry , ion , catalysis , combinatorial chemistry , organic chemistry , enantioselective synthesis , ecology , biology
All adducts one way : Iminium ions, generated in situ from the corresponding N,O‐acetals, can be used as electrophiles in a Morita–Baylis–Hillman‐type reaction with a wide range of Michael acceptors (enones, enals, S ‐ and O ‐acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate).

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