The bicyclo[3.3.1]nonane ring represents an attractive yet challenging synthetic targets in the field of organic synthesis, especially in a stereocontrolled fashion. Over the past two decades, organocatalysis has emerged as an enabling technology for the facile construction of enantioenriched molecules with remarkably increasing complexity and diversity, and a myriad of chiral architectures containing bicyclo[3.3.1]nonane units were elegantly assembled through organocatalytic asymmetric transformations. This review summarizes recent advancements on this topic (mainly from 2010 to 2023), emphasizing the reaction types such as desymmetrization and cascade reactions of different prochiral starting materials toward various chiral bicyclo[3.3.1]nonanes as well as their aza, oxa and thio derivatives. Meanwhile, the synthetic strategy, reaction mechanism, substrate scope and synthetic applications of these catalytic reactions are also discussed. We hope that this review will motivate further development and application of organocatalytic asymmetric synthesis of bicyclo[3.3.1]nonane frameworks.

中文翻译：

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双环[3.3.1]壬烷框架的有机催化不对称合成研究进展


双环[3.3.1]壬烷环代表了有机合成领域中一种有吸引力但具有挑战性的合成靶标，尤其是在立体控制方式下。在过去的二十年里，有机催化已成为一种易于构建对映体富集分子的使能技术，其复杂性和多样性显著增加，并且包含双环[3.3.1]壬烷单元的无数手性结构通过有机催化不对称转化优雅地组装。本文总结了该主题的最新进展（主要是 2010 年至 2023 年），重点介绍了不同原手性起始材料对各种手性双环[3.3.1]壬烷及其 aza、oxa 和 thio 衍生物的反应类型，如去对称和级联反应。同时，还讨论了这些催化反应的合成策略、反应机理、底物范围和合成应用。我们希望这篇综述将推动双环[3.3.1]壬烷框架的有机催化不对称合成的进一步开发和应用。