A Convenient Approach to the Synthesis of ω-Heterocyclic Amino Acids from Carboxy Lactams through Ring-Chain Transformation; Part 1: Synthesis of (2S)-/(2R)-2-Amino-4-(1-aryl-/1,5-diaryl-1H-pyrazol-3-yl)butyric Acid

Abstract

A general method is reported for the synthesis of ω-heterocyclic α-amino acids, which involves preparation of enaminone intermediates from thiolactams, followed by reaction with dinucleophiles, resulting in a single-step condensation and ring-chain transformation to the desired ω-heterocyclic α-amino acids after deprotection of amine and carboxylic group. The reaction steps preserve the chirality of the parent-substituted lactam. The method is illustrated by the synthesis of (2S)- and (2R)-2-amino-4-(1-aryl-/1,5-diaryl-1H-pyrazol-3-yl)butyric acids.

Key words

amino acids - ring opening - chirality - lactams - hydrogenations

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