Rh(III)-Catalyzed Domino [4 + 2] Annulation/Aza-Michael Addition of <i>N</i>-(Pivaloyloxy)benzamides with 1,5-Enynes via C–H Activation: Synthesis of Functionalized Aromathecins
Chada Raji Reddy, Kathe Mallesh, Srinivas Bodasu, Ramachandra Reddy Donthiri
Abstract
Reported herein are the Rh(III)-catalyzed cascade annulation reactions of N-(pivaloyloxy)benzamides with 1,5-enynes to access diversely substituted aromathecin derivatives involving C–H activation. The developed procedure offers an efficient synthetic tool for the assembly of a wide range of N-(pivaloyloxy)benzamides and 1,5-enynes with good atom economy and functional group tolerance. The key reactions involved in this annulation are alkyne insertion and aza-Michael addition under oxidant-free mild reaction conditions.
Topics & Concepts
ChemistryAnnulationDominoCatalysisCombinatorial chemistryMichael reactionMedicinal chemistryStereochemistryOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Alkyne Reactions