Syntheses of α-Amino Squaric Acids Using an Aminomalonate Equivalent Bearing a Squaryl Group

Abstract

The synthesis of an amino acid analogue bearing a squaryl group as a carboxylic acid surrogate (sq-AA; 2) has been developed. Aminomalonate equivalent 6 was used as a nucleophilic synthon whose alkylation or conjugate addition reaction followed by deprotection and decarboxylation reaction gave sq-AAs.

amino acids - squaric acid - malonate - alkylations - addition reactions

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The Sq group is sensitive to strongly basic or acidic conditions, giving a complex mixture.

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