Access to Complex Scaffolds Through [2 + 2] Cycloadditions of Strained Cyclic Allenes
Matthew McVeigh, Jacob P. Sorrentino, Allison T. Hands, Neil K. Garg
Abstract
We report the strain-induced [2 + 2] cycloadditions of cyclic allenes for the assembly of highly substituted cyclobutanes. By judicious choice of trapping agent, complex scaffolds bearing heteroatoms, fused rings, contiguous stereocenters, spirocycles, and quaternary centers are ultimately accessible. Moreover, we show that the resulting cycloadducts can undergo thermal isomerization. This study provides an alternative strategy to photochemical [2 + 2] cycloadditions for accessing highly functionalized cyclobutanes, while validating the use of underexplored strained intermediates for the assembly of complex architectures.
Topics & Concepts
CyclobutanesChemistryHeteroatomStereocenterIsomerizationCycloadditionCombinatorial chemistryStereochemistryOrganic chemistryEnantioselective synthesisRing (chemistry)CatalysisCyclization and Aryne ChemistryCatalytic Alkyne ReactionsSynthetic Organic Chemistry Methods