Highly Stereospecific Cross-Coupling Reactions of Anomeric Stannanes for the Synthesis of C‑Aryl Glycosides

We demonstrate that configurationally stable anomeric stannanes undergo a stereospecific cross-coupling reaction with aromatic halides in the presence of a palladium catalyst with exceptionally high levels of stereocontrol. In addition to a broad substrate scope (>40 examples), this reaction elim...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2016-09, Vol.138 (37), p.12049-12052
Main Authors: Zhu, Feng, Rourke, Michael J, Yang, Tianyi, Rodriguez, Jacob, Walczak, Maciej A
Format: Article
Language:English
Subjects:
Catalysis
Glycosides - chemical synthesis
Molecular Structure
Palladium
Tin Compounds - chemistry
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Summary:We demonstrate that configurationally stable anomeric stannanes undergo a stereospecific cross-coupling reaction with aromatic halides in the presence of a palladium catalyst with exceptionally high levels of stereocontrol. In addition to a broad substrate scope (>40 examples), this reaction eliminates critical problems inherent to nucleophilic displacement methods and is applicable to (hetero)­aromatics, peptides, pharmaceuticals, common monosaccharides, and saccharides containing free hydroxyl groups.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b07891