Chiral Ligands Containing Heteroatoms; 12.1 Synthesis of Optically Active 2-Amino-2-(2′-pyridyl)-1-alkanols from β-Hydroxy-α-amino Acids

Sergio Cossu; Sandra Conti; Giampaolo Giacomelli; Massimo Falorni

doi:10.1055/s-1994-25707

Synthesis 1994; 1994(12): 1429-1432
DOI: 10.1055/s-1994-25707

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Chiral Ligands Containing Heteroatoms; 12.¹ Synthesis of Optically Active 2-Amino-2-(2′-pyridyl)-1-alkanols from β-Hydroxy-α-amino Acids

Sergio Cossu^* , Sandra Conti, Giampaolo Giacomelli, Massimo Falorni

^*Dipartimento di Chimica, Università degli Studi di Sassari, Via Vienna 2, I-07100 Sassari, Italy

Abstract

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The synthesis of a new class of optically active ligands such as the title compounds is presented. All the multistep procedures adopted start by the conversion of L-serine and L-threonine into the proper 2,2-dimethyloxazolidines, followed by transformation of the corresponding nitriles to pyridines. The reaction sequence occurs without loss of enantiomeric purity and with overall satisfactory yield.

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