Garratt–Braverman Cyclization, a Powerful Tool for C–C Bond Formation
Garratt–Braverman Cyclization, a Powerful Tool for C–C Bond Formation
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DOI：
10.1055/s-0032-1317321
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发表时间：
2012-10
期刊：
影响因子：
2
通讯作者：
Sayantan Mondal;Tapobrata Mitra;Raja Mukherjee;P. Addy;A. Basak
中科院分区：
文献类型：
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作者：
Sayantan Mondal;Tapobrata Mitra;Raja Mukherjee;P. Addy;A. Basak
摘要 C-C 键形成新策略的开发仍然处于有机合成的前沿。通过原位生成的双丙二烯，双炔丙基砜的碱基介导重排，现在称为 Garratt-Braverman 环化 (GBC)，导致形成两个新的 C-C 键。由于广泛的范围和有趣的机制，该反应最近引起了有机化学家的关注。本报告旨在介绍该领域的发展，特别强调合成应用。 1 简介 2 双自由基生成反应 3 双自由基的命运 4 Garratt-Braverman 环化；历史发展 5 Garratt-Braverman 化学在有机合成中的探索 5.1 Braverman 的工作 5.2 Feldman 的工作 5.3 作者组的贡献 6 GBC 与双自由基/协同环化反应之间的竞争 6.1 GBC 与 MSC/SC 6.2 GBC 与 6π 电环化 6.3 GBC 与亲核加成7 结论和未来展望
Abstract Development of new strategies for C–C bond formation remains in the forefront of organic synthesis. The base-mediated rearrangement of bis-propargyl sulfones via bis-allenes generated in situ, now known as the Garratt–Braverman cyclization (GBC), leads to the formation of two new C–C bonds. The reaction has recently drawn attention from organic chemists due to the wide scope as well as interesting mechanism. This report aims to give an account of the developments in this area with particular emphasis on synthetic applications. 1 Introduction 2 Biradical-Generating Reactions 3 Fate of Biradicals 4 Garratt–Braverman Cyclization; A Historical Development 5 Exploration of Garratt–Braverman Chemistry in Organic Synthesis 5.1 Braverman’s Work 5.2 Feldman’s Work 5.3 Contribution from the Author’s Group 6 Competition between GBC and Biradical/Concerted Cyclization Reactions 6.1 GBC vs. MSC/SC 6.2 GBC vs. 6π-Electrocyclization 6.3 GBC vs. Nucleophilic Addition 7 Conclusion and Future Aspects