Deoxyalkoxyamination of Alcohols for the Synthesis of N-Alkoxy-N-alkylbenzenesulfonamides

摘要

A novel protocol for the deoxyalkoxyamination of alcohols has been developed, using N-alkoxybenzenesulfonimide (NOSI) as both a sulfonyl transfer reagent and an alkoxyamine source, accessing a diverse range of N-alkoxy-N-alkylbenzenesulfonamides with excellent isolated yields. This method is characterized by metal-free reaction, scalability, and waste-balance. Chiral substrates are converted with excellent levels of stereochemical inversion. NOSI could be generated in situ during the reaction as a stable reagent if a three-component one-pot reaction was designed. Exploiting this approach to run intramolecular reactions offered various N-protected isoxazolidines. In addition,valuable O-alkyl hydroxylamines (or isoxazolidines) were obtained through a neutral strategy of desulfonylation of the products.