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首页> 外文期刊>Chemistry: A European journal >Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, and N-Methoxyamides
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Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, and N-Methoxyamides

机译：叔酰胺，仲酰胺和N-甲氧基酰胺的化学选择性还原亲核加成

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摘要

As the complexity of targeted molecules increases in modern organic synthesis, chemoselectivity is recognized as an important factor in the development of new methodologies. Chemoselective nucleophilic addition to amide carbonyl centers is a challenge because classical methods require harsh reaction conditions to overcome the poor electrophilicity of the amide carbonyl group. We have successfully developed a reductive nucleophilic addition of mild nucleophiles to tertiary amides, secondary amides, and N-methoxyamides that uses the Schwartz reagent [Cp2ZrHCl]. The reaction took place in a highly chemoselective fashion in the presence of a variety of sensitive functional groups, such as methyl esters, which conventionally require protection prior to nucleophilic addition. The reaction will be applicable to the concise synthesis of complex natural alkaloids from readily available amide groups.
机译：随着目标分子在现代有机合成中的复杂性增加，化学选择性被认为是开发新方法的重要因素。酰胺羰基中心的化学选择性亲核加成是一个挑战，因为经典方法需要苛刻的反应条件以克服酰胺羰基的不良亲电性。我们已经成功开发了使用Schwartz试剂[Cp2ZrHCl]将轻度亲核试剂​​还原成亲核性三元酰胺，仲酰胺和N-甲氧基酰胺的方法。该反应在各种敏感的官能团，例如甲酯的存在下，以高度化学选择性的方式发生，这些官能团通常需要在亲核加成之前进行保护。该反应将适用于由容易获得的酰胺基团简单合成复杂的天然生物碱。

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