Short and efficient syntheses of functionalized (pyrrolidin-2-yl)phosphonate and (5-oxopyrrolidin-2-yl)phosphonate have been developed. The synthetic strategy involved the diastereospecific 1,3-dipolar cycloaddition of N-benzyl-C-(diethoxyphosphoryl)nitrone to cis-1,4-dihydroxybut-2-ene and dimethyl maleate, respectively. O,O-Diethyl 3-carbamoyl-4-hydroxy(5-oxopyrrolidin-2-yl)phosphonate was obtained from O,O-diethyl 2-benzyl-4,5-dimethoxycarbonyl(isoxazolidin-3-yl)phosphonate by hydrogenation and subsequent treatment with ammonia, whereas transformation of O,O-diethyl 2-benzyl-4,5-dihydroxymethyl(isoxazolidin-3-yl)phosphonate into O,O-diethyl 3-aminomethyl-4-hydroxy(pyrrolidin-2-yl)phosphonate was accomplished by mesylation followed by hydrogenolysis to undergo intramolecular cyclization and the introduction of amino group via ammonolysis. Stereochemistry of the isoxazolidine cycloadducts, as well as the final functionalized (pyrrolidin-2-yl)- and (5-oxopyrrolidin-2-yl)phosphonates were established based on conformational analyses using vicinal H–H, H–P, and C–P couplings and supported by the observed diagnostic NOESY correlation signals.

中文翻译：

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官能化的（吡咯烷基-2-基）膦酸二乙酯和（5-氧吡咯烷基-2-基）膦酸二乙酯的合成

已经开发了短而有效的官能化的（吡咯烷-2-基）膦酸酯和（5-氧代吡咯烷-2-基）膦酸酯的合成方法。的合成策略涉及的diastereospecific 1,3-偶极环加成Ñ苄基Ç - （二乙氧基磷酰基）硝酮向顺式-1,4- dihydroxybut -2-烯和马来酸二甲酯，分别。ø，ø -二乙基-3-氨基甲酰基-4-羟基（5-氧代吡咯烷-2-基）从得到的膦酸酯ø，ö通过氢化二乙基-2-苄基-4,5-二甲氧基（异恶唑烷-3-基）膦酸酯和随后用氨水处理，而O，O的转化二乙基2-苄基-4,5-二羟基（异恶唑烷-3-基）膦酸为Ô，ø -二乙基-3-氨甲基-4-羟基（吡咯烷-2-基）膦，通过甲磺酰化，接着完成通过氢经历分子内环化和通过氨解引入氨基。基于邻位H–H，H–P和C–的构象分析，建立了异恶唑烷环加合物的立体化学以及最终官能化的（吡咯烷-2-基）-和（5-氧吡咯烷-2-基）膦酸酯P耦合并由观察到的诊断NOESY相关信号支持。