Atroposelective Synthesis of Axially Chiral Biaryls by Palladium‐Catalyzed Asymmetric C−H Olefination Enabled by a Transient Chiral Auxiliary

Atroposelective synthesis of axially chiral biaryls by palladium‐catalyzed C−H olefination, using tert‐leucine as an inexpensive, catalytic, and transient chiral auxiliary, has been realized. This strategy provides a highly efficient and straightforward access to a broad range of enantioenriched bia...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-06, Vol.56 (23), p.6617-6621
Main Authors: Yao, Qi‐Jun, Zhang, Shuo, Zhan, Bei‐Bei, Shi, Bing‐Feng
Format: Article
Language:English
Subjects:
atropisomerism
biaryls
kinetic resolution
Leucine
olefination
Optical activity
Palladium
Selectivity
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Summary:Atroposelective synthesis of axially chiral biaryls by palladium‐catalyzed C−H olefination, using tert‐leucine as an inexpensive, catalytic, and transient chiral auxiliary, has been realized. This strategy provides a highly efficient and straightforward access to a broad range of enantioenriched biaryls in good yields (up to 98 %) with excellent enantioselectivities (95 to >99 % ee). Kinetic resolution of trisubstituted biaryls bearing sterically more demanding substituents is also operative, thus furnishing the optically active olefinated products with excellent selectivity (95 to >99 % ee, s‐factor up to 600). No attachements: The title reaction employs tert‐leucine as a transient chiral auxiliary and provides efficient access to enantioenriched biaryls in good yields (up to 98 %) with excellent enantioselectivities (up to >99 % ee). Kinetic resolution of trisubstituted biaryls bearing sterically more demanding substituents is also operative, thus furnishing the optically active olefinated products with excellent selectivity (up to >99 % ee, s‐factor up to 600).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201701849