Reactions of Iminium Ions with Michael Acceptors through a Morita–Baylis–Hillman‐Type Reaction: Enantiocontrol and Applications in Synthesis | Zendy

Myers Eddie L. | Zendy; de Vries Johannes G. | Zendy; Aggarwal Varinder K. | Zendy

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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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