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. 2009 Feb 19;11(4):807-10.
doi: 10.1021/ol802325h.

Mitsunobu approach to the synthesis of optically active alpha,alpha-disubstituted amino acids

Jonathan E Green  1 , David M Bender, Stona Jackson, Martin J O'Donnell, James R McCarthy
Affiliations

Mitsunobu approach to the synthesis of optically active alpha,alpha-disubstituted amino acids

Jonathan E Green et al. Org Lett. .

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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