Stereochemical Studies. XXI. Studies on α-Alkyl-α-amino Acids. XV. Application of Thermal Isocyanide-Cyanide Rearrangement to R-S Conversion of α-Methylphenylalanine

Abstract

R-S Conversion of R (+)-α-methylphenylalanine (R (+)-V), one of the typical α-alkyloc-amino acids, was accomplished with 75.6% retention of its optical integrity, since the R (+)-isocyanide (R (+)-X) easily derived from R (+)-V afforded the S (+)-cyanide (S (+)-XI) with 75.6% retention of configuration when a diphenyl ether solution of R (+)-X was heated at 280°.
Preliminary experiments using racemic compounds were also reported in experimental part.