TITLE:
An Efficient Synthesis of 2,3-Diaminoacid Derivatives Using Phosphine Catalyst
AUTHORS:
Yohei Oe, Hiroaki Kishimoto, Nahoko Sugioka, Daisuke Harada, Yukio Sato, Tetsuo Ohta, Isao Furukawa
KEYWORDS:
Addition, Alkynes, Amino Acids, Catalysis, Multi-Component Reaction
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.4 No.3,
September
17,
2014
ABSTRACT: Ethyl 2,3-diphthalimidoylpropanoate was effectively synthesized from ethyl propynoate with two equivalents of phthalimide catalyzed by triphenylphosphine in good yield. The choice of reaction media was important for selective synthesis of the desired 2,3-diaminocarboxylic acid derivatives. The reaction is considered to occur through a zwitterionic intermediate derived from the reaction of the α,β-unsaturated ester with triphenylphosphine.