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Solid-Phase Synthesis of N-Aminodipeptides in High Optical Purity
A.-S. Felten, R. Vanderesse, N. Brosse, C. Didierjean, B. Jamart-Grégoire*
21 February 2008 (online)
A solid-phase synthesis of N-aminodipeptide derivatives via the Mitsunobu protocol was developed. Thus, the reaction of (S)-α-hydroxy acids 1 with a Wang resin using DIC followed by the deprotection of the resulting THP esters 2 gave the α-hydroxy esters 3. The Mitsunobu reaction of 3 with (S)-α-aminohydrazine phthalimide 4 afforded the polymer-supported esters 5. TFA-mediated cleavage of 5 gave the N-aminodipeptide derivatives 6a-j in 21-55% yield with excellent diastereomeric purity (>95% de).