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首页> 外文期刊>RSC Advances >Functionalization of α-hydroxyphosphonates as a convenient route to N-tosyl-α-aminophosphonates
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Functionalization of α-hydroxyphosphonates as a convenient route to N-tosyl-α-aminophosphonates

机译：α-羟基膦酸酯的官能化是N-甲苯磺酰基-α-氨基膦酸酯的便捷途径

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摘要

Direct conversion of the α-hydroxyl group by para -toluenesulfonamide to yield α-( N -tosyl)aminophosphonates is reported. α-Aminophosphonates 23a,b–37a,b were obtained from the corresponding α-hydroxyphosphonates 6a,b–21a,b in the presence of K _(2) CO _(3) , via the retro-Abramov reaction of the appropriate aldehydes, 1–5 . The subsequent formation of imines with simultaneous addition of diethyl phosphite provided access to the α-sulfonamide phosphonates 23a,b–37a,b with better diastereoselectivity than in the case of the Pudovik reaction. The mechanism for this transformation is proposed herein. When Cbz N -protected aziridine 9a,b and phenylalanine analogue 12a,b were exploited, intramolecular substitution was observed, leading to the corresponding epoxide 38 as the sole product, or oxazolidin-2-one 39 as a minor product. Analogous substitution was not observed in the case of proline 18a,b and serine 21a,b derivatives.
机译：据报道，对甲苯磺酰胺将α-羟基直接转化为α-（N-甲苯磺酰基）氨基膦酸酯。通过在适当的醛的逆阿布拉莫夫反应下，在K _（2）CO _（3）存在下，从相应的α-羟基膦酸酯6a，b-21a，b获得α-氨基膦酸酯23a，b–37a，b。 ，1–5。随后形成亚胺并同时加入亚磷酸二乙酯使获得α-磺酰胺膦酸酯23a，b-37a，b的方法具有比Pudovik反应更好的非对映选择性。本文提出了这种转换的机制。当利用Cbz N-保护的氮丙啶9a，b和苯丙氨酸类似物12a，b时，观察到分子内取代，导致相应的环氧化物38为唯一产物，或恶唑烷-2-酮39为次要产物。在脯氨酸18a，b和丝氨酸21a，b衍生物的情况下未观察到类似的取代。

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