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Novel approach to the synthesis of aliphatic and aromatic alpha-keto acids

2012-09, Balducci, Daniele, Conway, Philip A., Sapuppo, Giulia, Müller-Bunz, Helge, Paradisi, Francesca

A new practical and efficient synthesis of alpha-keto acids was accomplished starting from the synthon 1,4-diacetylpiperazine-2,5-dione. The synthesis encompasses both aromatic and aliphatic substrates proving to be versatile and innovative with excellent carbon economy and recycling of the glycine by-product.

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One-step diketopiperazine synthesis using phase transfer catalysis

2009-04-15, O'Reilly, Elaine, Lestini, Elena, Balducci, Daniele, Paradisi, Francesca

A simple and efficient one-step procedure is described for the synthesis of a number of symmetrical 1,4-disubstituted piperazine-2,5-diones under phase transfer conditions. The reactions are carried out at room temperature, starting from a suitable N-chloroacetamide in the presence of an aqueous solution of sodium hydroxide. Piperazine-2,5-diones were obtained with excellent selectivity in yields of up to 90%.

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A stereoselective synthesis of α-deuterium labelled (S)-α-amino acids

2010, O'Reilly, Elaine, Balducci, Daniele, Paradisi, Francesca

An atom-efficient and stereoselective synthesis has been developed for the preparation of a-2H-labelled(S)-a-amino acids, starting from a novel chiral diketopiperazine scaffold. Efficient mono-alkylation of the chiral template afforded the (S)-substituted adducts with the nature of the electrophile significantly effecting the stereochemical outcome. Subsequent alkylation was totally selective producing the 1,4-cis adduct as the sole diastereoisomer. The deprotection was carried out using cerium ammonium nitrate followed by acid hydrolysis affording the enantipure a-amino acids.