We report herein a highly straightforward strategy for the synthesis of a new axially chiral 3-arylindolizine scaffold via organocatalytic asymmetric arylation reactions of indolizines and p-quinone esters. Using the chiral phosphoric acid catalyst, a series of axially chiral 3-arylindolizines were accessed in good to excellent yields and atropo-enantioselectivities. This approach features a broad substrate scope, mild reaction conditions, good scalability, and facile derivatization. Moreover, preliminary investigations based on nonlinear effects and a thermal racemization study demonstrated the intrinsic pathway for the formation of axial chirality and its potential utility.
An organocatalytic highly diastero-and enantioselective Friedel−Crafts conjugate addition of indolizines to prochiral cyclopentenediones has been successfully developed. This desymmetric transformation provides a direct access to the desired indolizine-substituted cyclopentanediones in yields of 62−91% and excellent stereoselectivities. The utility of the approach was demonstrated by diverse late-stage functionalizations through reduction or oxidation. Importantly, the direct sp 2 C−H functionalization with nitromethane in one-pot process resulted in the indolizine-linked axially chiral styrene bearing a remote chiral center.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.