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首页> 外文期刊>RSC Advances >Pyrrolidine and oxazolidine ring transformations in proline and serine derivatives of alpha-hydroxyphosphonates induced by deoxyfluorinating reagents
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Pyrrolidine and oxazolidine ring transformations in proline and serine derivatives of alpha-hydroxyphosphonates induced by deoxyfluorinating reagents

机译：通过脱氧氟化试剂诱导的丙氨酸和氧化胺和恶唑烷烃环转化和甲羟基亚膦酸酯的α-羟基膦酸盐衍生物

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摘要

Transformations of alpha-hydroxyphosphonates derived from proline or serine by treatment with different deoxyfluorinating reagents (DAST, Deoxofluor, PyFluor) are reported. Depending on the applied reagent, as well as the protecting group used (N-Cbz, N-Boc, N-Bn) different types of products are observed. The reaction of N-Cbz or N-Boc prolinols with DAST or Deoxofluor due to aziridinium intermediate participation gave fluorinated amino phosphonates such as piperidine and pyrrolidine derivatives and/or oxazolidine-2-ones. Similarly, the analogous reaction of N-Cbz or N-Boc protected serinol yielded oxazolidine-2-ones or its fluorinated analogues. As the second type of product formed by DAST-induced reaction of serine derivatives, aziridines were obtained. Only in the case of deoxyfluorination of N-benzyl prolinols were both diastereoisomers of beta-fluoropiperidine-alpha-phosphonates formed, while the reaction of protected N-benzyl serinols gave fluorinated oxazolidines. Moreover, application of PyFluor gave sulfonate derivatives.
机译：通过用不同的脱氧氟化试剂（DAST，Deoxofluor，Pyfluor）向衍生自脯氨酸或丝氨酸衍生自脯氨酸或丝氨酸的α-羟基膦酸酯的转化。根据所施加的试剂，以及所用的保护基（N-CBZ，N-BOC，N-BN）不同类型的产品。 N-CBZ或N-BOC脯氨酸与脂肪醌中间体参与引起的荷叶氟喹啉的反应产生氟化氨基膦酸，如哌啶和吡咯烷衍生物和/或恶唑烷-2-酮。类似地，N-CBZ或N-BOC保护钠的类似反应产生恶唑烷 - 2-苯酚或其氟化类似物。作为由诸如尿素衍生物反应形成的第二种类型的产物，得到氮化物。只有在N-苄基脯氨酸的脱氧氟化的情况下，β-氟哌啶-α-膦酸的两种非对映异构体，而受保护的N-苄基丝醇的反应产生氟化恶唑烷。此外，Pyfluor对磺酸盐衍生物的应用。

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  • 来源
    《RSC Advances》 |2018年第43期|共14页
  • 作者

    Kaczmarek Patrycja; Rapp Magdalena; Koroniak Henryk;

  • 作者单位

    Adam Mickiewicz Univ Fac Chem Umultowska 89b PL-61614 Poznan Poland;

    Adam Mickiewicz Univ Fac Chem Umultowska 89b PL-61614 Poznan Poland;

    Adam Mickiewicz Univ Fac Chem Umultowska 89b PL-61614 Poznan Poland;

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  • 正文语种 eng
  • 中图分类 化学;
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