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 eliminates critical problems inherent to nucleophilic displacement methods and is applicable to (hetero)aromatics, peptides, pharmaceuticals, common monosaccharides, and saccharides containing free hydroxyl groups.
Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80309, United States.
Feng
F
Zhu
Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80309, United States.
Michael J
MJ
Rourke
Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80309, United States.
Tianyi
T
Yang
Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80309, United States.
Jacob
J
Rodriguez
Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80309, United States.
Maciej A
MA
Walczak
D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium; D017971:Tin Compounds / Q000737:chemistry*
D006027:Glycosides; D017971:Tin Compounds; D010165:Palladium