Development and synthetic applications of asymmetric [3,3]-sigmatropic rearrangments
Development and synthetic applications of asymmetric [3,3]-sigmatropic rearrangments
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DOI：
10.2174/1385272013375526
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发表时间：
2001-04-01
影响因子：
2.6
通讯作者：
Baird, RD
中科院分区：
文献类型：
--
作者：
Allin, SM;Baird, RD
在这篇综述中，我们试图让读者对现在以更流行的不对称[3,3]-符号位重排而闻名的许多合成应用有所了解。预测重排的立体化学结果的能力，以及制备含有几个连续手性中心的产品的能力，使得这种不对称重排的应用对合成化学家来说是一个有吸引力的命题。我们和其他人已经开始开发armine-Cope重排作为一种新的合成方案，它似乎有很多未开发的潜力。重排是通过逐步的还是协调的机制进行的，以及这种机制途径是否可以控制，这些问题仍有待确定。我们小组目前的工作旨在将不对称氨基- cope重排应用于合成有用的程序，例如在高官能化氧和氮杂环的合成中。我们将适时报告这方面的进展。
In this review we have sought to g,ive the reader an appreciation of the many synthetic applications now known for the more popular asymmetric [3,3]-sigmatropic rearrangements. The ability to predict the stereochemical outcome of the rearrangements, and the ability to prepare products containing several contiguous chiral centres makes the application of such asymmetric rearrangements an attractive proposition to the synthetic chemist.We, and others, have begun to develop the armine-Cope rearrangement as a new synthetic protocol that appears to have much untapped potential. The question of the whether the rearrangement proceeds via a stepwise or concerted mechanism, and if the mechanistic pathway can be controlled, remains to be established. Current work in our group is aimed at applying the asymmetric amino-Cope rearrangement in synthetically useful procedures, for example in the synthesis of highly functionalised oxygen and nitrogen heterocycles. Our progress in this area will be reported in due course.