• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>Chemistry: A European journal >A Three-Component Reaction for Diversity-Oriented Synthesis of Polysubstituted Piperidines: Solution and Solid-Phase Optimization of the First Tandem Aza[4+2]/Allylboration
【24h】

A Three-Component Reaction for Diversity-Oriented Synthesis of Polysubstituted Piperidines: Solution and Solid-Phase Optimization of the First Tandem Aza[4+2]/Allylboration

机译：多元定向合成多取代哌啶的三组分反应：第一串氮杂[4 + 2] /烯丙基硼化的溶液和固相优化

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

This article describes the design and optimization of a simple three-component aza[4+2]/allylboration reaction to access polysubstiuted alpha-hydroxy-alkyl piperidines in a highly diastereo-controlled fashion from maleimidees, 4-boronhyrazonodienes, and aldehydes. The aldehyde component does not interfere with the first aza[4+2] step, and it was found that this tandem reaction provides better yields of piperidine products 5 when carried out in one-pot. The required 4-borono-hydrazono-dienes 1 are synthesized efficiently from the condensation of 3-boronoacrolein pinacol ester (4) with hydrazines. Overall, the three-component process using N-substituted maleimides as dienophiles produces four stereogenic centers and is quite generl. It tolerates the use of a wide variety of aldehydes and hydrazine precursors with different electronic and steric characteristics. By allowing such a wide substrate scope and up to four elements of diversity, this reaction process is particularly well adapted towards applicatioins in diversity-oriented synthesis of polysubstituted piperidine derivatives. The suitability of the aza[4+2]/allylboration reaction for use in solid-phase chemistry was also demonstrated using a N-arylmaleidobenzoic cid functionalized resin. This novel multicomponent reaction thus offers a high level of stereocontrol and versaility in the preparation of densely functionalized nitrogen heterocycles.
机译：本文介绍了一种简单的三组分aza [4 + 2] /烯丙基化反应的设计和优化，该反应以高度非对映体控制的方式从马来酰亚胺，4-硼hy并二烯和醛中获得多取代的α-羟基-烷基哌啶。醛组分不干扰第一步氮杂[4 + 2]步骤，并且发现当在一个锅中进行时，该串联反应提供了更高产率的哌啶产物5。所需的4-硼烷-肼基二烯1是由3-硼烷丙烯醛频哪醇酯（4）与肼缩合而有效合成的。总的来说，使用N-取代的马来酰亚胺作为亲二烯体的三组分过程产生了四个立体异构中心，并且相当通用。它容许使用具有不同电子和空间特性的各种醛和肼前体。通过允许如此宽的底物范围和多达四个多样性的元素，该反应过程特别适合于在多取代的哌啶衍生物的多样性导向的合成中的应用。氮杂[4 + 2] /烯丙基化反应在固相化学中的适用性也通过使用N-芳基马来基苯甲酸Cid官能化树脂得到了证明。因此，这种新颖的多组分反应在制备致密官能化的氮杂环化合物中提供了高水平的立体控制和多功能性。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号