Tetrahedron: Asymmetry

Synthesis of a water-soluble chiral NMR shift reagent:(S)-PDTA

N Florini, GF Arnaud, B Kónya, C Zucchi, G Pályi

Index: Florini, Nicola; Arnaud, Gaelle F.; Konya, Balint; Zucchi, Claudia; Palyi, Gyula Tetrahedron Asymmetry, 2009 , vol. 20, # 9 p. 1036 - 1039

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Citation Number: 12

Abstract

A five-step synthesis of the water-soluble chiral polydentate ligand,(S)-PDTA [(S)-PDTA= N, N, N′, N′-tetrakis [(hydroxycarbonyl) methyl]-(S)-1, 2-diaminopropane] starting from l- alanine has been worked out, via steps with retention of chirality. Total yield is 50.7%(average of∼ 88% for each step), while published methods report 33.4% total yield over four steps.