Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India.
J Org Chem. 2022 Aug 19;87(16):11073-11089. doi: 10.1021/acs.joc.2c01324. Epub 2022 Aug 10.
A novel methodology for redox-neutral [4 + 1] annulation of unactivated alkenes with sulfoxonium ylides leads to the synthesis of a diverse library of indanone compounds. The developed annulation reaction was found to be highly versatile due to its compatibility with various unactivated alkenes functionalized with various sensitive functional groups as well as substituted sulfoxonium ylides. Further, multiple transformations such as ring-expansion, reduction, aldol condensation, and Wittig reaction were carried out with indanones. Using this way, highly useful cyclic heterocycles such as indene, dihydroisocoumarin, and 1-indanilidene were prepared in a single step. A possible reaction mechanism was supported by deuterium labeling studies, competitive studies, and kinetic isotopic studies.
一种新型的氧化还原中性[4+1]环化反应方法，用于未活化的烯烃与亚砜叶立德的反应，可合成各种茚酮化合物。该发展的环化反应具有高度的通用性，因为它与各种带有各种敏感官能团以及取代的亚砜叶立德的未活化烯烃相兼容。此外，还对茚酮进行了多种转化，如扩环、还原、羟醛缩合和Wittig 反应。通过这种方式，可以一步制备高度有用的环状杂环化合物，如茚、二氢异香豆素和 1-茚甲亚胺。氘标记研究、竞争研究和动力学同位素研究支持了可能的反应机制。
