Synthesis of (S)- and (R)-1-(2-furyl)alkylamines and (S)- and (R)-alpha-amino acids through the addition of organometallic reagents to imines derivedfrom (S)-valinol

(S)-1-(2-Furyl)alkylamines were prepared through the addition of organometa llic reagents to the imine derived from 2-furaldehyde and (S)-valinol, prev ious protection of the auxiliary hydroxy group as trimethylsilyl ether, fol lowed by removal of the auxiliary. Then, protection of the primary amine as tosylamide or benzamide and oxidation of the furan ring gave the N-derivat ives of (S)-alpha-amino acids. (R)-N-Benzoylphenylglycine was prepared from the benzaldimine, where the hydroxy group was protected as the tert-butyld imethylsilyl ether, through addition of 2-furyllithium.