Preparation of <i>Z</i>-α,β-Unsaturated Diazoketones from Aldehydes. Application in the Construction of Substituted Dihydropyridin-3-ones
作者:Isac G. Rosset、Antonio C. B. Burtoloso
DOI:10.1021/jo401191s
日期:2013.9.20
The stereoselective preparation of α,β-unsaturated diazoketones with Z geometry is described from aldehydes and a new olefination reagent. When prepared from amino aldehydes, these diazoketones could be converted to substituted dihydropyridin-3-ones in just one step, after an intramolecular N–H insertion reaction. The straightforward synthesis of a natural trihydroxylated piperidine demonstrates the
从醛和一种新的烯烃化试剂描述了具有Z几何形状的α,β-不饱和重氮酮的立体选择性制备。当由氨基醛制备时,在分子内NH插入反应后,仅一步即可将这些重氮酮转化为取代的二氢吡啶-3-酮。天然三羟基化哌啶的直接合成证明了这些不饱和重氮酮对哌啶的快速构建的实用性。