Mitsunobu Approach to the Synthesis of Optically Active α,α-Disubstituted Amino Acids
2009-02-19T00:00:00Z (GMT) by
Chiral tertiary α-hydroxy esters of known stereochemical configuration were transformed to α-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 α-carbon. Several α,α-disubstituted amino acids were synthesized in high overall chemical yield and optical purity.
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