Preparation of Z-alpha,beta-Unsaturated Diazoketones from Aldehydes. Application in the Construction of Substituted Dihydropyridin-3-ones

作者：Rosset Isac G; Burtoloso Antonio C B^*

来源：Journal of Organic Chemistry, 2013, 78(18): 9464-9470.

DOI：10.1021/jo401191s

The stereoselective preparation of alpha,beta-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 utility of these unsaturated diazoketones for the rapid construction of piperidines.

• 出版日期2013-9-20