170940-99-5Relevant articles and documents
Synthesis of chiral diazanedicarboxylate and diazenedicarboxylate esters: electrophilic amination reactions of achiral ester and amide enolates
Harris, Joanna M.,Bolessa, Evon A.,Mendonca, Aubrey J.,Feng, Sheng-Chu,Vederas, John C.
, p. 1945 - 1950 (2007/10/02)
A series of chiral dialkyl (bornyl, isobornyl, menthyl) diazenedicarboxylates 4a-c were prepared by conversion of the corresponding alcohols into chloroformates, condensation with hydrazine, and oxidation of the corresponding dialkyl diazanedicarboxylates 3a-c with N-bromosuccinimide and pyridine (50-90percent yield).Their reaction with achiral enolates of esters and N,N-dimethyl amides at -70 deg C gave α-hydrazino acid derivatives with little or no stereoselectivity.Analogous amination of chiral oxazolidinone (Evans enolate) anions were highly selective, but were controlled exclusively by enolate geometry.