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Deoxyalkoxyamination of Alcohols for the Synthesis of N ‐Alkoxy‐ N ‐alkylbenzenesulfonamides
Author(s) -
Sun QiAn,
Lu ZeHai,
Pu XiaoQiu,
Hu HuiLian,
Zhang Jiaheng,
Yang XianJin
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800526
Subject(s) - chemistry , reagent , alkoxy group , combinatorial chemistry , intramolecular force , alkyl , sulfonyl , organic chemistry
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.