
%0 Journal Article
%A Hartshorn, RM 
%T Chelated 2-Formylglycinate: Aldehyde or Enol?
%J Australian Journal of Chemistry
%D 1996/08/01
%V 49
%N 8
%P 905-909
%K 
%R https://doi.org/10.1071/CH9960905
%U https://www.publish.csiro.au/paper/CH9960905 
%X 13 C n.m.r. data are presented which are consistent with the proposal that 2-formylglycinate chelated to bis(ethane-1,2-diamine)cobalt(III) exists as an equilibrium mixture of its hydrate, 3,3-dihydroxyalaninate (c.90%), and its E-enol , (E)-2-amino-3-hydroxyacrylate (c.10%). The new structural assignment for the minor component of the mixture leads to the proposal of a new mechanism for the formation of coordinated penicilloates by reaction of this mixture with (S)-penicillamine . The new mechanism makes it possible to rationalize the remarkable stereoselectivity of this condensation reaction. 
