Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from L-proline

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Abstract

Diastereoselective introduction of phosphono groups into l-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Benzoyl-l-prolinate preferentially gave trans-phosphorylated products, which could be easily transformed into (S)-(pyrrolidin-2-yl)phosphonates. On the other hand, N-benzyloxycarbonyl-l- prolinate reacted with phosphite to give cis-substituted products, which could be easily transformed into (R)-(pyrrolidin-2-yl)phosphonates. © 2011 Elsevier Ltd. All rights reserved.

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Hirata, S., Kuriyama, M., & Onomura, O. (2011). Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from L-proline. Tetrahedron, 67(48), 9411–9416. https://doi.org/10.1016/j.tet.2011.09.080

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