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- Title
Enantiodivergent Atroposelective Synthesis of Chiral Biaryls by Asymmetric Transfer Hydrogenation: Chiral Phosphoric Acid Catalyzed Dynamic Kinetic Resolution.
- Authors
Mori, Keiji; Itakura, Tsubasa; Akiyama, Takahiko
- Abstract
Reported herein is an enantiodivergent synthesis of chiral biaryls by a chiral phosphoric acid catalyzed asymmetric transfer hydrogenation reaction. Upon treatment of biaryl lactols with aromatic amines and a Hantzsch ester in the presence of chiral phosphoric acid, dynamic kinetic resolution (DKR) involving a reductive amination reaction proceeded smoothly to furnish both R and S isomers of chiral biaryls with excellent enantioselectivities by proper choice of hydroxyaniline derivative. This trend was observed in wide variety of substrates, and various chiral biphenyl and phenyl naphthyl adducts were synthesized with satisfactory enantioselectivities in enantiodivergent fashion. The enantiodivergent synthesis of synthetically challenging, chiral o-tetrasubstituted biaryls were also accomplished, and suggests high synthetic potential of the present method.
- Subjects
PHOSPHORIC acid; TRANSFER hydrogenation; KINETIC resolution; ENANTIOSELECTIVE catalysis; SUBSTRATES (Materials science); THERMAL oxidation (Materials science); BIPHENYL compounds
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 38, p11642
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201606063