Chiral diene-promoted room temperature conjugate arylation: highly enantioselective synthesis of substituted chiral phenylalanine derivatives and α,α-di(arylmethyl)acetates

A highly enantiocontrolled room temperature rhodium-catalyzed conjugate arylation process was developed. The reaction proceeds through 1,4-addition of α-substituted acrylates followed by enantioselective protonation using a C 1 -symmetric chiral bicyclo[2,2,2] diene as the ligand and water as the pr...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-06, Vol.18 (24), p.4569-4574
Main Authors: Chen, Jian-Ping, Xu, Ming-Hua
Format: Article
Language:English
Subjects:
Acetates
Acetic acid
Acrylates
Catalysis
Conjugates
Crystallography
Derivatives
Enantiomers
Phenylalanine
Protonation
Rhodium
Room temperature
Substitutes
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Summary:A highly enantiocontrolled room temperature rhodium-catalyzed conjugate arylation process was developed. The reaction proceeds through 1,4-addition of α-substituted acrylates followed by enantioselective protonation using a C 1 -symmetric chiral bicyclo[2,2,2] diene as the ligand and water as the proton source. This exceptionally simple protocol provides a reliable and practical access to structurally important phenylalanine derivatives and α,α-di(arylmethyl)acetates in high yields (up to 99%) with good to excellent ee values (up to 99%). A highly enantiocontrolled room temperature rhodium-catalyzed conjugate arylation process for practical synthesis of enantioenriched phenylalanine derivatives and α,α-di(arylmethyl)acetates is described.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00616e