Recent advances in phosphine-mediated sequential annulations

IF 9.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chinese Chemical Letters Pub Date : 2024-11-09 DOI:10.1016/j.cclet.2024.110628

Xuling Pan, Wei Cai, You Huang

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Abstract

Polycyclic compounds are widely found in natural products and drug molecules with important biological activities, which attracted the attention of many chemists. Phosphine-catalyzed nucleophilic addition is one of the most powerful tools for the construction of various cyclic compounds with the advantages of atom economy, mild reaction conditions and simplicity of operation. Allenolates, Morita−Baylis−Hillman (MBH) alcohols and their derivatives (MBHADs), electron-deficient olefins and alkynes are very efficient substrates in phosphine mediated annulations, which formed many phosphonium species such as β-phosphonium enolates, β-phosphonium dienolates and vinyl phosphonium ylides as intermediates. This review describes the reactivities of these phosphonium zwitterions and summarizes the synthesis of polycycle compounds through phosphine-mediated intramolecular and intermolecular sequential annulations. Thus, a systematic summary of the research process based on the phosphine-mediated sequential annulations of allenolates, MBH alcohols and MBHADs, electron-deficient olefins and alkynes are presented in Chapters 2–6, respectively.

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膦介导序贯环的最新进展

多环化合物广泛存在于天然产物和药物分子中，具有重要的生物活性，引起了许多化学家的关注。膦催化的亲核加成反应具有原子经济、反应条件温和、操作简单等优点，是构建各种环类化合物的有力手段之一。烯丙酸酯、Morita - Baylis - Hillman （MBH）醇及其衍生物（MBHADs）、缺电子烯烃和炔烃是磷化氢介导环中非常有效的底物，形成了许多磷物质，如β-烯醇化磷、β-二烯醇化磷和乙烯基酰化磷作为中间体。本文综述了这些磷两性离子的反应活性，并对膦介导的分子内和分子间序环合成多环化合物的研究进展进行了综述。因此，基于膦介导的烯丙酸酯、MBH醇和MBHADs、缺电子烯烃和炔烃的顺序环的研究过程分别在第2-6章中进行了系统的总结。

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来源期刊

Chinese Chemical Letters 化学-化学综合

CiteScore

14.10

自引率

15.40%

发文量

8969

审稿时长

1.6 months

期刊介绍： Chinese Chemical Letters (CCL) (ISSN 1001-8417) was founded in July 1990. The journal publishes preliminary accounts in the whole field of chemistry, including inorganic chemistry, organic chemistry, analytical chemistry, physical chemistry, polymer chemistry, applied chemistry, etc.Chinese Chemical Letters does not accept articles previously published or scheduled to be published. To verify originality, your article may be checked by the originality detection service CrossCheck.