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Catalytic, Enantioselective α‐Alkylation of Azlactones with Nonconjugated Alkenes by Directed Nucleopalladation
Author(s) -
Nimmagadda Sri Krishna,
Liu Mingyu,
Karunananda Malkanthi K.,
Gao DeWei,
Apolinar Omar,
Chen Jason S.,
Liu Peng,
Engle Keary M.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814272
Subject(s) - enantioselective synthesis , alkene , chemistry , alkylation , regioselectivity , catalysis , phosphoric acid , tsuji–trost reaction , organic chemistry , combinatorial chemistry
A palladium(II)‐catalyzed enantioselective α‐alkylation of azlactones with nonconjugated alkenes is described. The reaction employs a chiral BINOL‐derived phosphoric acid as the source of stereoinduction, and a cleavable bidentate directing group appended to the alkene to control the regioselectivity and stabilize the nucleopalladated alkylpalladium(II) intermediate in the catalytic cycle. A wide range of azlactones were found to be compatible under the optimal reaction conditions to afford products bearing α,α‐disubstituted α‐amino‐acid derivatives with high yields and high enantioselectivity.