α-Phenylglycinol as chiral auxiliary in diastereoselective Strecker synthesis of α-amino acids

Article abstract of DOI:10.1016/0040-4020(95)00523-B

The high diastereoselectivity achieved in Strecker synthesis using inexpensive α-phenylglycinol as chiral auxiliary and its facile removal by oxidative clearange make it an ideal choice for the large scale preparations of optically active α-amino acids specially α-arylglycines present abundantly in glycopeptide antibiotics. A number of chiral amino acids are synthesized following this method. Also molecular mechanics calculations are carried out to explain the observed diastereoselection.