Novel one carbon-carbon bond formation: An efficient preparation of stereospecific beta-hydroxy nitriles

ORGN 141

Sheila Marie H. Jacobo, sjacobo@fit.edu1, Mustafa Adiyaman2, Chih Tsung Chang1, Nam-In Kang1, William S. Powell3, and Joshua Rokach1. (1) Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 W. University Blvd., Melbourne, FL 32901, (2) Organize Sanayani Bolgesi, Eczacibasi Fine Chemical Products, Fatih Cad. No. 12, Cerkezkoy, Tekirdag, 59500, Turkey, (3) Meakins-Christie Laboratories and Department of Medicine, McGill University, 3626 St-Urbain St., Montreal QC, H2 X 2P2, Canada
The cyanide-ring opening of thionocarbonates with NaCN in DMF and TBACN in THF is described. This reaction occured regioselectively to afford beta-hydroxy nitrile with preserved stereochemistry of the hydroxy group in high yield.