Parmentier, Michael, Baudoin, Olivier, Antien, Kevin and Geraci, Andrea (2021) A New Dioxazolone for the Synthesis of 1,2-Aminoalcohols via Iridium(III)-Catalyzed C(sp3)–H Amidation. Angewandte Chemie International Edition. ISSN 1433-78511521-3773

Abstract

Vicinal aminoalcohols are widespread structural motifs in bioactive molecules. We report the development of a new dioxazolone reagent containing a p-nitrophenyldifluoromethyl group, which 1. displays a good safety profile; 2. shows a remarkably high reactivity in the oxime-directed iridium(III)-catalyzed amidation of unactivated C(sp3)–H bonds; 3. leads to amide products which can be hydrolyzed under mild conditions. The amidation reaction is mild, general and compatible with both primary C–H bonds of tertiary and secondary alcohols, as well as secondary C–H bonds of cyclic secondary alcohols. This method provides an easy access to free 1,2-aminoalcohols after efficient and mild cleavage of the oxime directing group and activated amide.

Item Type:	Article
Keywords:	amidation • 1,2-amino alcohol • C–H activation • dioxazolone • iridium
Date Deposited:	07 Sep 2021 00:45
Last Modified:	07 Sep 2021 00:45
URI:	https://oak.novartis.com/id/eprint/45287