Stereospecific Suzuki cross-coupling of alkyl alpha-cyanohydrin triflates.
Scalemic alpha-cyanohydrin triflates undergo Pd-catalyzed cross-coupling with aryl, heteroaryl, 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 achieves a higher level of molecular complexity than the products of traditional Suzuki reactions.
He
Anyu
A
Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA.
Falck
J R
JR
D002384:Catalysis; D009570:Nitriles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D009570:Nitriles; C430593:cyanohydrin; D010165:Palladium