Tandem Sequences Involving Michael Additions and Sigmatropic Rearrangements
Tandem Sequences Involving Michael Additions and Sigmatropic Rearrangements
复制标题
涉及迈克尔加成和西格玛重排的串联序列
DOI：
10.1055/s-0035-1562554
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发表时间：
2016
期刊：
影响因子：
--
通讯作者：
A. Martín
中科院分区：
文献类型：
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作者：
D. Serrano;A. Martín
摘要 Claisen 和相关的 [3,3]-σ 重排已被充分描述为有用的合成有机工具。通常，[3,3]-σ重排与串联序列中的其他反应组合，导致仅在一个合成步骤中形成多个键。这篇综述介绍了结合共轭迈克尔型加成和[3,3]-σ重排的串联序列的最相关进展。介绍了使用不同类型的亲核试剂引发串联序列的相关例子，以及说明在制备合成有用的构建模块中标题序列的使用的详细评论。还提供了基于这些串联序列的催化方法的例子。最后，详细介绍了用于合成光学活性γ-取代δ-氨基酸的逆串联[3,3]-重排/迈克尔加成序列的不对称版本。 1 简介 2 Michael 加成/[3,3]-重排序列 2.1 C-亲核试剂 2.2 N-亲核试剂 2.3 P-亲核试剂 2.4 O-亲核试剂 3 [3,3]-重排/Michael 加成序列 4 结论
Abstract Claisen and related [3,3]-sigmatropic rearrangements have been well described as useful synthetic organic tools. Frequently, the [3,3]-sigmatropic rearrangements are combined with other reactions in a tandem sequence leading to the formation of several bonds in only one synthetic step. This review presents the most relevant advances in tandem sequences combining a conjugate Michael-type addition and a [3,3]-sigmatropic rearrangement. Relevant examples of the use of different types of nucleophiles initiating the tandem sequences, along with detailed commentary illustrating the use of the title sequences in the preparation of synthetically useful building blocks, are presented. Examples of catalytic methodologies based on these tandem sequences are also provided. Finally, the asymmetric version of an inverse tandem [3,3]-rearrangement/Michael addition sequence oriented to the synthesis of optically active γ-substituted δ-amino acids is detailed. 1 Introduction 2 Michael Addition/[3,3]-Rearrangement Sequences 2.1 C-Nucleophiles 2.2 N-Nucleophiles 2.3 P-Nucleophiles 2.4 O-Nucleophiles 3 [3,3]-Rearrangement/Michael Addition Sequences 4 Conclusion