Stereospecific Suzuki Cross-Coupling of Alkyl α-Cyanohydrin Triflates
Anyu He and J. R. Falck*
*Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390, Email: j.falckutsouthwestern.edu
A. He, J. R. Falck, J. Am. Chem. Soc., 2010, 132, 2524-2525.
DOI: 10.1021/ja910582n (free Supporting Information)
α-Cyanohydrin triflates undergo Pd-catalyzed cross-coupling with aryl and vinyl boronic acids under mild conditions. Coupling proceeds with complete inversion of configuration at the stereogenic carbon. The resultant nitrile can be easily converted into a variety of alternative functional groups of value in organic synthesis and thus a high level of molecular diversity can be achieved.
see article for more examples