A new synthetic strategy toward nonracemic phosphoryl-substituted pyrrolidines and tetrahydropyranes with three and five contiguous stereocenters is presented. Readily available β-keto phosphonates react with conjugated nitroolefins in the presence of a chiral Ni(II) complex to give nitro keto phosphonates with two stereocenters with excellent enantioselectivity and moderate to high diastereoselectivity. These products were used for a reductive cyclization leading to pyrrolidin-3-ylphosphonic acid and for reactions with aldehydes yielding tetrahydropyranylphosphonates as individual stereoisomers. These nonracemic heterocycles containing phosphoryl moieties are useful for designing new pharmacologically active compounds.

中文翻译：

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从Ni（II）催化的Michael反应的非外消旋加合物中方便地获得具有多个连续立体中心的吡咯烷-3-基膦酸和四氢-2H-吡喃-3-基膦酸酯。

提出了一种新的合成策略，针对具有三个和五个连续立体中心的非外消旋磷酸基取代的吡咯烷和四氢吡喃。在手性Ni（II）络合物的存在下，易得的β-酮膦酸酯与共轭硝基烯烃反应，得到具有两个立体中心的硝基酮膦酸酯，具有出色的对映选择性和中等至高非对映选择性。这些产物用于还原环化反应生成吡咯烷基-3-基膦酸，并与醛反应生成四氢吡喃基膦酸酯作为单独的立体异构体。这些含有磷酰基部分的非外消旋杂环可用于设计新的药理活性化合物。