Department of Chemistry and Biochemistry, Baylor University, Waco, TX, 76798, USA.
Angew Chem Int Ed Engl. 2016 Nov 2;55(45):13934-13943. doi: 10.1002/anie.201602217. Epub 2016 Sep 21.
Although acylammonium salts are well-studied, chiral α,β-unsaturated acylammonium salts have received much less attention. While these intermediates are convenient synthons, which are readily available from several commodity unsaturated acids and acid chlorides, and possess three reactive sites, their application in organic synthesis has been limited because of the lack of appropriate chiral Lewis bases for their generation. In recent years, the utility of chiral, unsaturated acylammonium salts has expanded considerably, thus demonstrating the unique reactivity of this intermediate leading to the development of a diverse array of catalytic, asymmetric transformations including organocascade processes. This Minireview highlights the recent and growing interest in these intermediates which might spark further research into their untapped potential for asymmetric organocascade catalysis. A cursory comparison is made to related unsaturated iminium and acylazolium intermediates.
尽管酰基铵盐得到了广泛研究，但手性α,β-不饱和酰基铵盐却受到较少关注。尽管这些中间体是方便的合成子，可从几种商品不饱和酸和酰氯容易获得，并具有三个反应位点，但由于缺乏合适的手性路易斯碱来生成它们，其在有机合成中的应用受到限制。近年来，手性不饱和酰基铵盐的用途大大扩展，从而证明了这种中间体的独特反应性可导致多种催化、不对称转化的发展，包括有机级联过程。这篇综述强调了人们对手性不饱和酰基铵盐的兴趣日益浓厚，这可能会激发对其未开发的不对称有机级联催化潜力的进一步研究。与相关的不饱和亚胺和酰唑啉中间体进行了简要比较。
