Synthesis of Indanones and Spiroindanones by Diastereoselective Annulation Based on a Hydrogen Autotransfer Strategy
Yate Chen, Zhengtian Ding, Yiming Wang, Wenfeng Liu, Wangqing Kong
Abstract
An unprecedented nickel-catalyzed domino reductive cyclization of alkynes and o-bromoaryl aldehydes is described. The reaction features broad substrate scope and is tolerant of a variety of functional groups, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio- and diastereoselectivity. Preliminary mechanistic studies have shown that indanones are formed by the cyclization of o-bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.
Topics & Concepts
ChemistryAnnulationPyrrolidineCombinatorial chemistryFunctional groupCatalysisDominoReaction conditionsSubstrate (aquarium)Organic chemistryPolymerGeologyOceanographyCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis of Indole Derivatives