Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies,Asian Journal of Organic Chemistry

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Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2017-07-04 , DOI: 10.1002/ajoc.201700202
Jong-Wha Jung ₁ , Seok-Ho Kim ₂ , Young-Ger Suh ₂

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The aza‐Claisen rearrangement, also known as the 3‐aza‐Cope rearrangement, has attracted significant attention because it can be used as a complimentary method to access a diverse range of useful organic molecules. The presence of a nitrogen atom at the 3‐position enables the tethering of various‐sized azacycles, thereby giving ring‐expansion strategies that take advantage of the aza‐Claisen rearrangement a distinct advantage compared to other [3,3]‐sigmatropic rearrangements. Recent advances in aza‐Claisen rearrangements have facilitated otherwise‐inaccessible ring expansions in a highly stereoselective manner. The utility of aza‐Claisen‐rearrangement‐induced ring‐expansion strategies has been exemplified in the synthesis of a diverse range of natural products. This Focus Review summarizes recent advances in aza‐Claisen‐rearrangement‐induced ring‐expansion strategy, in particular applications in the synthesis of bioactive alkaloids.

中文翻译：

Aza-Claisen重排诱导环扩展策略的进展

氮杂-克莱森重排，也称为3-氮杂-科普重排，已引起了广泛的关注，因为它可以作为一种补充方法来使用各种有用的有机分子。在3位氮原子的存在使各种大小的氮杂环的束缚成为可能，因此与其他[3,3]σ重排相比，利用氮杂-克莱森重排的扩环策略具有明显的优势。氮杂-克莱森（Aza-Claisen）重排的最新进展以高度立体选择性的方式促进了原本难以接近的环扩展。在各种天然产物的合成中已举例说明了氮杂-克莱森重排诱导的环扩环策略的效用。

更新日期：2017-07-04

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