Enantioselective, Palladium-Catalyzed Conjugate Additions
of Arylboronic Acids to Form Bis-benzylic Quaternary Stereocenters
Version 2 2017-07-21, 20:33
Version 1 2017-07-21, 20:10
Posted on 2017-07-21 - 20:33
We report enantioselective,
palladium-catalyzed conjugate additions
of arylboronic acids to β-aryl, β,β-disubstituted
enones to generate ketones containing bis-benzylic quaternary stereocenters.
A catalyst generated from palladium trifluoroacetate and (S)-4-tert-butyl-2-(2-pyridyl)oxazoline
ligand ((S)-t-BuPyOx) promotes conjugate
additions of a wide range of arylboronic acids to a variety of β-aryl,
β,β-disubstituted enones. Iterative addition of the arylboronic
acid to minimize undesired protodeboronation pathways leads to efficient
formation of the corresponding ketones containing bis-benzylic quaternary
stereocenters in up to 92% yield and up to 93% enantioselectivity.
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Kadam, Abhishek
A.; Ellern, Arkady; Stanley, Levi M. (2017). Enantioselective, Palladium-Catalyzed Conjugate Additions
of Arylboronic Acids to Form Bis-benzylic Quaternary Stereocenters. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b01825
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AUTHORS (3)
AK
Abhishek
A. Kadam
AE
Arkady Ellern
LS
Levi M. Stanley