Facile synthesis of both enantiomers of (pyrrolidin-2-yl)phosphonate from l-proline |
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Authors: | Shigeo HirataMasami Kuriyama Osamu Onomura |
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Institution: | Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan |
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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. |
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Keywords: | Diastereoselective phosphorylation Arbusov reaction (Pyrrolidin-2-yl)phosphonate l-Proline" target="_blank">l-Proline |
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