Enantiospecific synthesis of allylamines via the regioselective rhodium-catalyzed allylic amination reaction
Enantiospecific synthesis of allylamines via the regioselective rhodium-catalyzed allylic amination reaction
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DOI：
10.1021/ja991089f
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发表时间：
1999-07-21
影响因子：
15
通讯作者：
Nelson, JD
中科院分区：
文献类型：
--
作者：
Evans, PA;Robinson, JE;Nelson, JD
作者已经接受了报道刘易斯酸促进反应进展的挑战。这一地区的活动十分活跃，特别是在1980年代和1990年代初。由于这一领域的信息太多，作者将其范围限制在(1)Lewis酸-羰基配合物，(2)Lewis酸促进的烯反应，(3)Lewis酸促进的烯丙基硅烷和烯丙基硅烷与醛酮的加成反应，(4)Lewis酸促进的缩醛取代反应，(5)Sakurai反应（烯丙基硅烷和烯丙基锡烷与烯酮的共轭加成），以及(6)Lewis酸促进的Diels-Alder反应。尽管关注点较窄，但这仍然是一项艰巨的任务，而且他们已经令人钦佩地完成了这项任务。第1章介绍了刘易斯酸羰基相互作用及其理论方面。其余章节涵盖了在复杂有机化合物的立体选择性合成中已被证明有用的特定反应。每一章都以历史介绍和机械考虑开始。在相关的情况下，对热反应和路易斯酸促进的反应进行了比较。接着是1993年以前的文献中组织良好的例子，重点是立体选择反应。第2章和第6章很好地介绍了手性路易斯酸在烯和Diels-Alder反应中的应用。作者们在总结他们所选择的转化的路易斯酸促进反应的进展方面做得很好。除了一些尴尬的时刻（可能是由于翻译），写作清晰，易于理解。由于材料太多，一些解释必须简短。该指数很短，但有一个单独的刘易斯酸指数作为补偿。唯一的小缺点是参考资料有点过时。有了一些最近的作品的集合，一个全面的文档就在手边了。总的来说，这本书将是一个极好的补充到研究生和从业者的图书馆有机合成。
The authors have taken up the challenge of covering the progress in Lewis acid-promoted reactions. There was an intense activity in this area, especially in the 1980s and early 1990s. Due to the amount of information in this area, the authors have restricted their coverage to (1) Lewis acid-carbonyl complexes,(2) Lewis acid-promoted ene reaction,(3) Lewis acid-promoted allylsilanes and allystannanes addition to aldehydes and ketones,(4) Lewis acid-promoted acetal substitution reactions,(5) the Sakurai reaction (conjugate additions of allylsilane and allylstannane to enones), and (6) Lewis acid-promoted Diels-Alder reactions. Despite the narrower focus, this is still a formidable task, and one they have met admirably. Chapter 1 covers Lewis acidcarbonyl group interactions and their theoretical aspects. The remaining chapters cover specific reactions that have been shown to be useful in stereoselective synthesis of complex organic compounds. Each chapter starts with a historical introduction and mechanistic considerations. Where relevant, comparisons of thermal and Lewis acid-promoted reactions have been made. This is followed by well-organized examples from the literature up to 1993, with the emphasis on stereoselective reactions. Chapters 2 and 6 have good coverage of the use of chiral Lewis acids for ene and Diels-Alder reactions. The authors have done an excellent job of summarizing the advances in Lewis acid-promoted reactions for the transformations they have chosen. Except for some awkward moments (probably due to the translation), the writing is clear and easy to follow. The amount of material necessitates that some explanations be brief. The index is short but is compensated by a separate Lewis acid index. The only minor drawback is that the references are somewhat dated. With a collection of some of the more recent works, a comprehensive documentation would be at hand. Overall, this book would be an excellent addition to the library of graduate students and practitioners of organic synthesis.