Polarization of the Pyridine Ring: Highly Functionalized Piperidines from Tungsten−Pyridine Complex,Journal of the American Chemical Society

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Polarization of the Pyridine Ring: Highly Functionalized Piperidines from Tungsten−Pyridine Complex
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2010-12-08 , DOI: 10.1021/ja107536w
Daniel P. Harrison ₁ , Michal Sabat ₁ , William H. Myers ₁ , W. Dean Harman ₁

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The N-acetylpyridinium complex of {TpW(NO)(PMe3)} undergoes regio- and stereoselective reactions with a broad range of common organic nucleophiles, providing a family of 1,2-dihydropyridine (DHP) complexes of the form TpW(NO)(PMe3)(3,4-η(2)-DHP). The present study explores the elaboration of these systems into novel piperidines. The addition of an acid to the DHP complexes generates highly asymmetric π-allyl complexes that in turn react with a second nucleophile at either C3 or C5. The subsequent oxidative decomplexation of these materials yields several piperidinamides with unconventional substitution patterns.

中文翻译：

吡啶环的极化：来自钨-吡啶络合物的高度官能化的哌啶

{TpW(NO)(PMe3)} 的 N-乙酰吡啶鎓配合物与多种常见的有机亲核试剂发生区域和立体选择性反应，提供了一系列 TpW(NO) 形式的 1,2-二氢吡啶 (DHP) 配合物(PMe3)(3,4-η(2)-DHP)。本研究探索将这些系统细化为新型哌啶。将酸添加到 DHP 复合物中会产生高度不对称的 π-烯丙基复合物，进而与 C3 或 C5 处的第二个亲核试剂反应。这些材料随后的氧化去络合产生了几种具有非常规取代模式的哌啶酰胺。

更新日期：2010-12-08

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