69874-73-3Relevant academic research and scientific papers
A practical aryl unit for azlactone dynamic kinetic resolution: Orthogonally protected products and a ligation-inspired coupling process
Tallon, Sean,Manoni, Francesco,Connon, Stephen J.
, p. 813 - 817 (2015/02/19)
The first strategy for bringing about enantioselective azlactone dynamic kinetic resolution to generate orthogonally protected amino acids has been developed. In the presence of a C2-symmetric squaramide-based catalyst, benzyl alcohol reacts with novel yet readily prepared tetrachloroisopropoxycarbonyl-substituted azlactones to generate trapped phthalimide products of significant synthetic interest with excellent enantiocontrol. These materials are masked amino acids which are demonstrably orthogonally protected: cleavage of the phthalimide can be achieved in the presence of the ester and vice versa. This process could be utilized to bring about a highly stereoselective ligation-type coupling of protected serines (at stoichiometric loadings) with racemic azlactones derived from both natural and abiotic amino acids. After deprotection, a subsequent base-mediated Oa??N acyl transfer occurs to form a dipeptide.
Synthesis of Nα-tetrachlorophthaloyl (TCP)-protected amino acids under microwave irradiation (MWI)
Cros,Planas,Bardají
, p. 1313 - 1320 (2007/10/03)
A range of Nα-tetrachlorophthaloyl protected amino acids have been synthesized by an easy and efficient condensation procedure of the corresponding amino acid and tetrachlorophthaloyl anhydride under irradiation in an unmodified commercial microwave oven.
