Catalyst‐ and Base‐Free Asymmetric Synthesis of Functionalized Prolines via One‐Pot Cascade Reactions,Advanced Synthesis & Catalysis

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Catalyst‐ and Base‐Free Asymmetric Synthesis of Functionalized Prolines via One‐Pot Cascade Reactions
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-05-28 , DOI: 10.1002/adsc.202000453
Hyunkyung Cho ₁ , Jinju Kim ₁ , Jae Hyun Kim ₁ , Yeonghun Song ₁ , Sanghee Kim ₁

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A one pot, three‐step cascade reaction to provide functionalized proline derivatives was developed. The Michael addition reaction of N‐allylated proline and activated alkyne forms a zwitterionic intermediate that further undergoes cyclization and [2,3]‐rearrangement to provide Cα‐alkylated proline bicyclic derivatives. This transformation was highly stereoselective and the chirality of the N‐allylated prolines was completely transferred to the product via a C−N−C chirality transfer process. The developed reaction is operationally simple and does not require any reagents other than the substrates.

中文翻译：

通过一锅级联反应实现功能性脯氨酸的无催化剂和无碱不对称合成

开发了一种一锅三步级联反应以提供功能化的脯氨酸衍生物。N-烯丙基化的脯氨酸和活化炔烃的迈克尔加成反应形成两性离子中间体，该中间体进一步进行环化和[2,3]重排，以提供Cα-烷基化的脯氨酸双环衍生物。这种转化是高度立体选择性的，N-烯丙基化的脯氨酸的手性是通过C-NC手性转移过程完全转移到产物中的。产生的反应操作简单，除底物外不需要任何试剂。

更新日期：2020-07-29

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