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Updated: Jun 26, 2026

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
Published on: November 2, 2016
Mitsunobu approach to the synthesis of optically active alpha,alpha-disubstituted amino acids
Jonathan E Green1, David M Bender, Stona Jackson
1Eli Lilly & Co., Lilly Corporate Center, Indianapolis, Indiana 46285, USA.
Abstract:
Chiral tertiary alpha-hydroxy esters of known stereochemical configuration were transformed to alpha-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the alpha-carbon. Several alpha,alpha-disubstituted amino acids were synthesized in high overall chemical yield and optical purity.
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