36939-30-7Relevant academic research and scientific papers
General Light-Mediated, Highly Diastereoselective Piperidine Epimerization: From Most Accessible to Most Stable Stereoisomer
Shen, Zican,Walker, Morgan M.,Chen, Shuming,Parada, Giovanny A.,Chu, Duc M.,Dongbang, Sun,Mayer, James M.,Houk,Ellman, Jonathan A.
supporting information, p. 126 - 131 (2021/01/12)
We report a combined photocatalytic and hydrogen atom transfer (HAT) approach for the light-mediated epimerization of readily accessible piperidines to provide the more stable diastereomer with high selectivity. The generality of the transformation was explored for a large variety of di- to tetrasubstituted piperidines with aryl, alkyl, and carboxylic acid derivatives at multiple different sites. Piperidines without substitution on nitrogen as well as N-alkyl and aryl derivatives were effective epimerization substrates. The observed diastereoselectivities correlate with the calculated relative stabilities of the isomers. Demonstration of reaction reversibility, luminescence quenching, deuterium labeling studies, and quantum yield measurements provide information about the mechanism.
A Synthesis of α-Substituted Amines
Hwang, Yuing C.,Chu, Min,Fowler, Frank W.
, p. 3885 - 3890 (2007/10/02)
The reaction of amides with organolithium reagents followed by hydride reducing agents has been studied as a synthetic route to α-substituted amines.The stereochemistry of the amine has been observed to depend upon the nature of the reducing agent.
