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Direct Synthesis of Free α‑Amino Acids by Telescoping Three-Step Process from 1,2-Diols

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journal contribution
posted on 15.01.2019, 19:24 by Haruki Inada, Masatoshi Shibuya, Yoshihiko Yamamoto
A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.