Journal of Organic Chemistry p. 5294 - 5299 (1986)
Update date:2022-08-03
Topics: Synthesis Chiral Organic synthesis Experimental Practical (R)-Phthalimido aldehydes D-α-Amino acids D-mannitol
Mulzer, Johann
Angermann, Alfred
Schubert, Boris
Seilz, Carsten
A short and practical synthesis of five D-α-amino acids is described from D-mannitol as the chiral educt.The key steps in the sequence are (a) the erythro-selective addition of organometals to (R)-2,3-O-isopropylideneglyceralaldehyde, (b) the Mitsunobu inversion substituting N-phthalimide for hydroxyl, and (c) acetonide hydrolysis and glycol cleavage to give the N -phthaloyl-(R)-α-aminoaldehydes 7.These are oxidized under Jones conditions to give the N-protected amino acids 8.The examples investigated (alanine, aminobutyric acid, norvaline, and allyl- and vinylglycine) demonstrate the general applicability of the method.
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