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Palladium‐Catalyzed Construction of Quaternary Stereocenters by Enantioselective Arylation of γ‐Lactams with Aryl Chlorides and Bromides
Author(s) -
Jette Carina I.,
Geibel Irina,
Bachman Shoshana,
Hayashi Masaki,
Sakurai Shunya,
Shimizu Hideki,
Morgan Jeremy B.,
Stoltz Brian M.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814475
Subject(s) - stereocenter , enantioselective synthesis , aryl , electrophile , chemistry , palladium , catalysis , yield (engineering) , ligand (biochemistry) , combinatorial chemistry , quaternary carbon , organic chemistry , medicinal chemistry , alkyl , materials science , biochemistry , receptor , metallurgy
Herein, we report the first Pd‐catalyzed enantioselective arylation of α‐substituted γ‐lactams. Two sets of conditions were developed for this transformation, allowing for the use of either aryl chlorides or bromides as electrophiles. Utilizing a highly electron‐rich dialkylphosphine ligand we have been able to construct α‐quaternary centers in good yields (up to 91 % yield) and high enantioselectivities (up to 97 % ee ).