Photochemical Rearrangement of N -Mesyloxylactams: Stereospecific Formation of N -Heterocycles

作者：Alexandre Drouin, Dana K. Winter, Simon Pichette, Samuel Aubert‐Nicol, Jean Lessard, Claude Spino · 发表于：The Journal of Organic Chemistry · 年份：2010 · DOI：10.1021/jo101805q · 被引用次数：19 · 研究领域：Synthetic Organic Chemistry Methods、Synthesis and Catalytic Reactions、Catalytic C–H Functionalization Methods

N-Mesyloxylactams undergo an efficient ring-contraction to N-heterocycles of various ring sizes. Yields increase with the degree of substitution α to the carbonyl. The stereochemical information of a chiral migrating carbon is conserved making this reaction a synthetically useful complement to the well-known Hofmann, Curtius, Lossen, and Schmidt rearrangements.