Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation

The RuPHOX‐Ru catalyzed asymmetric hydrogenation of diaryl ketones has been established, providing the corresponding chiral diaryl methanols in up to 99% yield and 99% ee. The protocol could be performed on a gram‐scale with a relatively low catalyst loading (2000 S/C) and the resulting products all...

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Published inAdvanced synthesis & catalysis Vol. 365; no. 8; pp. 1275 - 1286
Main Authors Zhou, Jiayu, Ye, Jianxun, Zhang, Yang, Li, Zhaodi, Li, Jingjing, Liu, Delong, Zhang, Wanbin
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 25.04.2023
Wiley Subscription Services, Inc
Subjects
Asymmetric hydrogenation
Asymmetry
Chemistry
Chemistry, Applied
Chemistry, Organic
Chiral diaryl methanols
Deuterium
Diaryl ketones
Hydrogenation
Ketones
Physical Sciences
RuPHOX-Ru
Science & Technology
Synthesis
Diaryl ketones
ARYLATION
HYDROSILYLATION
Asymmetric hydrogenation
RuPHOX-Ru
ARYL TRANSFER-REACTIONS
HETEROARYL KETONES
ALDEHYDES
GAMMA-LACTONES
Chiral diaryl methanols
Synthesis
LIGANDS
REDUCTION
ENANTIOSELECTIVE HYDROGENATION
BENZOPHENONES
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Summary:The RuPHOX‐Ru catalyzed asymmetric hydrogenation of diaryl ketones has been established, providing the corresponding chiral diaryl methanols in up to 99% yield and 99% ee. The protocol could be performed on a gram‐scale with a relatively low catalyst loading (2000 S/C) and the resulting products allow for several useful transformations, in particular for the synthesis of chiral drugs, such as, (S)‐Orphenadrine and (S)‐Neobenodine. Deuterium labeling and control experiments revealed that the RuPHOX‐Ru‐catalyzed asymmetric hydrogenation is fully subject to hydrogenation with H2 as the sole hydrogen source.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300213