Catalytic Sulfamoylation of Alcohols with Activated Aryl Sulfamates

Autor:	Naoko Ichiishi, David K. Leahy, Koichi Murai, Scott J. Miller, Peter B Rapp
Rok vydání:	2019
Předmět:	Organic base 010405 organic chemistry Aryl Organic Chemistry Alcohol 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Reagent Physical and Theoretical Chemistry Selectivity Catalytic method
Zdroj:	Organic Letters. 22:168-174
ISSN:	1523-7052 1523-7060
Popis:	We report a new catalytic method for alcohol sulfamoylation that deploys electron-deficient aryl sulfamates as activated group transfer reagents. The reaction utilizes the simple organic base N-methylimidazole, proceeds under mild conditions, and provides intrinsic selectivity for 1° over 2° alcohols (up to >40:1 for certain nucleosides). The requisite aryl sulfamate donors are stable crystalline solids that can be readily prepared on a large scale. Mechanistic considerations support the intermediacy of HNSO2 "aza-sulfene" in the transfer reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::db95f5414193a95c941958e4478e4b2e https://doi.org/10.1021/acs.orglett.9b04119 Zobrazit plný text záznamu