γ-Amino vinyl sulfoxides in asymmetric synthesis. Synthesis of optically pure α-substituted β-amino nitriles

• DOI: 10.1016/j.tet.2008.10.037
• Publication Date: 2008-10-19T04:08:07Z
• Authors: Ricardo Alfaro; Francisco Yuste; Benjamín Ortiz; Rubén Sánchez-Obr...; José L. García Ruano
• Keywords: 01 natural sciences; 0104 chemical sciences

Abstract The synthesis of optically pure (E)- and (Z)-γ-amino vinyl sulfoxides derived from commercially available protected α-amino esters is reported. Hydrocyanation of the double bond with Et2AlCN is completely stereoselective and provides enantiomerically pure α-substituted β-amino nitriles with complete control of the configuration at the α-carbon being exerted by the sulfinyl group.