Synthesis of Unsaturated Carboxylic and Amino Acids of Adamantane Series with the Use of Organophosphorus Reagents

Sodium derivative of diethyl(3-amino-1-ethoxycarbonylpropane)phosphonic acid was obtained by reaction of triethyl phosphonoacetate with ethylene imine in the presence of sodium hydride. The compound obtained was brought into Horner-Emmons reaction with carbonyl derivatives of adamantane series to afford the corresponding unsaturated amino acids. From adamantanecarbonyl chlorides and triphenylphosphonium ethoxycarbonylmethylide were prepared new phosphorus acylylides that on thermolysis provide ethyl acetylenecarboxylates containing an adamantyl substituent.