Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.,Angewandte Chemie International Edition

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Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-10-19 , DOI: 10.1002/anie.201809799
Vladislav G Lisnyak ₁ , Tessa Lynch-Colameta ₁ , Scott A Snyder ₁

Affiliation

Even though there are dozens of biologically active 2-substituted and 2,6-disubstituted piperidines, only a limited number of approaches exist for their synthesis. Herein is described two Mannich-type additions to nitrones, one using β-ketoacids under catalyst-free conditions and another using methyl ketones in the presence of chiral thioureas, which can generate a broad array of such 2-substituted materials, as well as other ring variants, in the form of β-N-hydroxy-aminoketones. Both processes have broad scope, with the latter providing products with high enantioselectivity (up to 98 %). The combination of these methods, along with other critical steps, has enabled 8-step total syntheses of the 2,6-disubstituted piperidine alkaloids (-)-lobeline and (-)-sedinone.

中文翻译：

环硝酮的曼尼希型反应：对映选择性合成含哌啶生物碱的有效方法。

尽管有数十种具有生物活性的 2-取代和 2,6-二取代哌啶，但其合成方法却有限。本文描述了硝酮的两种曼尼希型加成，一种在无催化剂条件下使用β-酮酸，另一种在手性硫脲存在下使用甲基酮，这可以生成多种此类2-取代材料以及其他材料环变体，以β-N-羟基氨基酮的形式。这两种工艺都有广泛的适用范围，后者提供的产品具有高对映选择性（高达 98%）。这些方法与其他关键步骤的结合，使得 2,6-二取代哌啶生物碱 (-)-山楂碱和 (-)-sedinone 的 8 步全合成成为可能。

更新日期：2018-10-19

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