Catalytic Asymmetric Aza‐Diels‐Alder Reaction: Pivotal Milestones and Recent Applications to Synthesis of Nitrogen‐Containing Heterocycles,Advanced Synthesis & Catalysis

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Catalytic Asymmetric Aza‐Diels‐Alder Reaction: Pivotal Milestones and Recent Applications to Synthesis of Nitrogen‐Containing Heterocycles
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-01-21 , DOI: 10.1002/adsc.202001307
Sergei Zlotin ₁ , Maxim G. Vinogradov ₂ , Olga V. Turova ₂

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In this review, the pivotal achievements and recent advances in catalytic asymmetric aza‐DAR reported up to 2020 are retrospectively considered and their potency for enantioselective synthesis of useful chiral piperidine, quinoline, pyridazine, oxazine and oxadiazine derivatives and fused compounds of higher molecular complexity bearing these pharmacology‐relevant heterocyclic scaffolds is demonstrated. The reported data are systematized according both to key electron transfer modes (normal or invers electron demand reactions) and to main types of attainable heterocyclic products. Of significant attention are an analysis of activation strategies (complexation, enamine or enolate formation, H‐bonding, etc.) applicable to reactions with particular types of dienes and dienophiles and identification of plausible reaction pathways (either concerted or stepwise) over stereoselective cyclization processes. The review contains 310 references and 122 synthetic schemes.

中文翻译：

催化不对称氮杂-Diels-Alder反应：重要里程碑及其在合成含氮杂环化合物中的最新应用

本文综述了直到2020年报道的催化不对称氮杂DAR的关键成就和最新进展，并探讨了它们对映选择性合成有用的手性哌啶，喹啉，哒嗪，恶嗪和恶二嗪衍生物以及具有更高分子复杂性的熔融化合物的对映选择性的能力。这些药理学相关的杂环支架被证明。根据关键的电子传输模式（正电子或反电子需求反应）和可获得的杂环产物的主要类型，对报告的数据进行了系统化。对激活策略的分析（络合，烯胺或烯醇形成，氢键等）引起了极大的关注。）适用于与特定类型的二烯和亲二烯体的反应以及在立体选择性环化过程中确定合理的反应途径（一致或逐步）。该综述包含310个参考文献和122个合成方案。

更新日期：2021-03-16

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