Enantioselective synthesis of axially chiral 3-bromo-4-alkoxy-2,6-dimethyl-5-(naphthalen-1-yl)pyridines via an asymmetric Suzuki–Miyaura cross-coupling reaction

[Display omitted] •Axially chiral compounds are very important building motifs.•The Suzuki–Miyaura cross-coupling reaction is an often used protocol for biaryl synthesis.•A simple method is reported for the enantioselective synthesis of chiral mono naphthyl substituted pyridine derivatives.•Atropiso...

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Bibliographic Details
Published in:Tetrahedron letters 2016-10, Vol.57 (42), p.4713-4717
Main Authors: Pomarański, Piotr, Samanta, Sauvik, Roszkowski, Piotr, Maurin, Jan K., Czarnocki, Zbigniew
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Atropisomer
Chiral ligand
Enantiomeric excess
Palladium-catalyzed reaction
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Summary:[Display omitted] •Axially chiral compounds are very important building motifs.•The Suzuki–Miyaura cross-coupling reaction is an often used protocol for biaryl synthesis.•A simple method is reported for the enantioselective synthesis of chiral mono naphthyl substituted pyridine derivatives.•Atropisomeric enantiomers were visualized by NMR using a chiral solvating agent. A simple method is reported for the synthesis of chiral mono-naphthyl substituted pyridine derivatives in good yield and with good enantiomeric excess via the asymmetric Suzuki–Miyaura cross-coupling reaction of 3,5-dibromo-4-alkoxy-2,6-dimethylpyridine and naphthalen-1-ylboronic acid. The structure and absolute stereochemistry of 3-bromo-4-methoxy-2,6-dimethyl-5-(naphthalen-1-yl)pyridine were established by single-crystal X-ray analysis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.09.024