Tetrahedron: Asymmetry

A novel and simple method for the preparation of (R)-and (S)-pyrrolidine-2-phosphonic acids: phosphonic acid analogues of proline

B Kaboudin, J Kato, H Aoyama, T Yokomatsu

Index: Kaboudin, Babak; Kato, Jun-Ya; Aoyama, Hiroshi; Yokomatsu, Tsutomu Tetrahedron Asymmetry, 2013 , vol. 24, # 24 p. 1562 - 1566

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Citation Number: 3

Abstract

Abstract A simple and convenient method has been developed for the preparation of (R)- and (S)-pyrrolidine-2-phosphonic acids. The thermal reaction of proline with diethyl phosphite in the presence of benzaldehyde gave an N-benzyl derivative of diethyl pyrrolidine-2-phosphonate, which was transformed into two diastereomeric amides by sequential debenzylation and acylation with (+)-dibenzoyl-l-tartaric anhydride. The two ...