Department of Organic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata-, 700032, India.
Angew Chem Int Ed Engl. 2016 Jun 27;55(27):7756-60. doi: 10.1002/anie.201603809. Epub 2016 Jun 13.
An efficient method for the aerobic radical-cascade alkylation/cyclization of α,β-unsaturated amides to afford functionalized oxindoles with a C3 quaternary stereocenter is described. The process is based on the generation of valuable alkyl radicals through sustainable aerobic C-H activation of aldehydes followed by decarbonylation using O2 as the sole oxidant. This method features a broad substrate scope, inexpensive alkyl radical precursors, and convenient reagents. Finally, the method was successfully applied to the synthesis of alkyl analogues of tetrahydrofuranoindoline and (±)-esermethole.
描述了一种有效的方法，通过α，β-不饱和酰胺的有氧自由基级联烷基化/环化反应，以 C3 季立体中心为特征，得到官能化的氧化吲哚。该过程基于通过可持续的有氧 C-H 活化醛来生成有价值的烷基自由基，然后使用 O2 作为唯一氧化剂进行脱羰。该方法具有广泛的底物范围、廉价的烷基自由基前体和方便的试剂。最后，该方法成功地应用于四氢呋喃吲哚和（±）-esermethole 的烷基类似物的合成。
