Ruthenium-Catalyzed Atropoenantioselective Synthesis of Axial Biaryls via Reductive Amination and Dynamic Kinetic Resolution

The unprecedented ruthenium-catalyzed atropoenantioselective reductive amination of aldehydes with alkylamines via a cascade transfer hydrogenation and dynamic kinetic resolution strategy is described. This protocol features broad substrate scope and good functional group tolerance and allows the ra...

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Published inOrganic letters Vol. 20; no. 19; pp. 6284 - 6288
Main Authors Guo, Donghui, Zhang, Jianwei, Zhang, Bei, Wang, Jian
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.10.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC CATALYSIS
CHIRAL BIARYLS
HYDROGENATION
ARYL BOND FORMATION
ENANTIOSELECTIVE SYNTHESIS
NATURAL-PRODUCTS
ATROPOSELECTIVE SYNTHESIS
PRIMARY AMINES
METAL
BRONSTED ACID CATALYSIS
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Summary:The unprecedented ruthenium-catalyzed atropoenantioselective reductive amination of aldehydes with alkylamines via a cascade transfer hydrogenation and dynamic kinetic resolution strategy is described. This protocol features broad substrate scope and good functional group tolerance and allows the rapid assembly of axially chiral biaryls in good to high yields with high to excellent enantioselectivities. In addition, such structural motifs may have potential applications in enantioselective catalysis as chiral ligands or catalysts.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02785