Lewis base catalysis of the Mukaiyama directed aldol reaction: 40 years of inspiration and advances.
Lewis base catalysis of the Mukaiyama directed aldol reaction: 40 years of inspiration and advances.
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DOI：
10.1002/anie.201302084
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发表时间：
2013-08-26
期刊：
影响因子：
--
通讯作者：
Denmark SE
中科院分区：
文献类型：
--
作者：
Beutner GL;Denmark SE
自从1973年第一个具有里程碑意义的直接羟醛加成反应问世以来，非对映和对映体选择性的羟醛加成反应已被提升到命名和策略水平反应的稀有状态(Mukaiyama直接Aldol反应)。这种反应在立体选择性合成无数种有机化合物中的重要性，无论是天然的还是非天然的，怎么强调都不为过。然而，它对该领域的影响超出了在合成中令人印象深刻的应用。定向的羟醛反应已经成为立体控制和催化的新概念和新方法的肥沃试验场。这篇简短的综述提供了一个案例，说明如何将位置选择性、非对映选择性、对映体选择性和催化合并到一个统一的反应流形中来刺激Lewis碱催化的Aldol加成反应的发展。作者的实验室和Mukaiyama教授的实验室记录了这一过程的演变。
Since the landmark publications of the first directed aldol addition reaction in 1973, the site, diastereo-, and enantioselective aldol reaction has been elevated to the rarefied status of being both a named and a strategy-level reaction (the Mukaiyama directed aldol reaction). The importance of this reaction in the stereoselective synthesis of untold numbers of organic compounds, both natural and unnatural, cannot be overstated. However, its impact on the field extends beyond the impressive applications in synthesis. The directed aldol reaction has served as a fertile proving ground for new concepts and new methods for stereocontrol and catalysis. This Minireview provides a case history of how the challenges of merging site selectivity, diastereoselectivity, enantioselectivity, and catalysis into a unified reaction manifold stimulated the development of Lewis base catalyzed aldol addition reactions. The evolution of this process is chronicled from the authors’ laboratories as well as in those of Professor Teruaki Mukaiyama.
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