Stereoselective Kinugasa/Aldol Cyclization: Synthesis of Enantioenriched Spirocyclic β-Lactams
Alexa Torelli, Eun Seo Choi, Aurélien Dupeux, Marcel Nicolas Perner, Mark Lautens
Abstract
We report an enantioselective copper-catalyzed Kinugasa/aldol domino reaction. This strategy enables access to a range of spirocyclic β-lactam pyrrolidinones in a stereoselective fashion. Under mild reaction conditions, prochiral alkyne-tethered ketones are coupled with nitrones to enable the facile construction of two spirofused ring systems containing three continuous stereocenters with excellent enantioselectivity. Also disclosed are post-transformation modifications demonstrating potential downstream functionalization of the spirocyclic molecules.
Topics & Concepts
StereocenterChemistryStereoselectivityAldol reactionEnantioselective synthesisDominoPyrrolidinonesLactamCombinatorial chemistryAlkyneRing (chemistry)Formal synthesisStereochemistryStereoisomerismMoleculeCatalysisOrganic chemistrySynthesis of β-Lactam CompoundsSynthetic Organic Chemistry MethodsSynthesis and Catalytic Reactions