Synthesis 2006(23): 4013-4016  
DOI: 10.1055/s-2006-950314
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of C-Protected 2,2-Dideutero β3-Amino Acids

Annalisa Guaragna*, Silvana Pedatella, Vittoria Pinto, Giovanni Palumbo
Università di Napoli Federico II, Dipartimento di Chimica Organica e Biochimica, Via Cynthia 4, 80126 Napoli, Italy
Fax: +39(081)674119; e-Mail: guaragna@unina.it;
Further Information

Publication History

Received 2 August 2006
Publication Date:
12 October 2006 (online)

Abstract

A simple three-step procedure for the preparation of C-protected 2,2-2H-β3-amino acids has been developed starting from the natural α-amino acids. Our synthetic path is based on the homologation reaction of α-amino acids through the formation of dideuterated alcohol intermediates obtained by heavy isotope reduction (NaBD4) of the carboxylic function.

11

Unpublished results.

12

β-Amino acids can be subdivided into β3, β2, and β2,3 amino acids, depending upon the position of the side chain(s) on the aminoalkanoic acid skeleton.

16

Ph3P-iodine complex showed the same reactivity of the polymer bound/iodine complex towards all the tested amino acids.