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Regio‐ and Stereoselective Modification of Chiral α‐Amino Ketones by Pd‐Catalyzed Allylic Alkylation
Author(s) -
Huwig Kai,
Schultz Katharina,
Kazmaier Uli
Publication year - 2015
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.201502975
Subject(s) - stereoselectivity , tsuji–trost reaction , alkylation , catalysis , allylic rearrangement , chemistry , organic chemistry
Chiral α‐amino ketones are excellent nucleophiles for stereoselective palladium‐catalyzed allylic alkylations. Both chiral as well as achiral allylic substrates can be applied, while the stereochemical outcome of the reaction is controlled by the chiral ketone enolate. The substituted amino ketones formed can be reduced stereoselectively, and up to five consecutive stereogenic centers can be obtained. This approach can be used for the synthesis of highly substituted piperidine derivatives.