Chemoselective Oxidation of Equatorial Alcohols with N-Ligated λ³-Iodanes.

ABSTRACT: The site-selective and chemoselective functionalization of alcohols in complex polyols remains a formidable synthetic challenge. Whereas significant advancements have been made in selective derivatization at the oxygen center, chemoselective oxidation to the corresponding carbonyls is less developed. In cyclic systems, whereas the selective oxidation of axial alcohols is well known, a complementary equatorial selective process has not yet been reported. Herein we report the utility of nitrogen-ligated (bis)cationic λ³-iodanes (N-HVIs) for alcohol oxidation and their unprecedented levels of selectivity for the oxidation of equatorial over axial alcohols. The conditions are mild, and the simple pyridine-ligated reagent (Py-HVI) is readily synthesized from commercial

SUBMITTER: Mikhael M 

PROVIDER: S-EPMC7060929 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature