Rh(iii)-Catalyzed C–H allylation/annulative Markovnikov addition with 5-methylene-1,3-dioxan-2-one: formation of isoquinolinones containing a C3 quaternary centre

Abstract

The Rh(III)-catalyzed synthesis of isoquinolinones containing a C3 quaternary centre via a tandem C–H allylation/annulative Markovinkov addition reaction has been achieved. This method employing a single Rh(III) complex as the catalyst tolerated various functional groups, and was applicable to late-stage diversification of N-methoxyamides derived from steroids and adapalene. By applying the protocol as the key step, US28 inverse agonist analogs were conveniently synthesized.