Highly Selective Synthesis of Seven-Membered Azaspiro Compounds by a Rh(I)-Catalyzed Cycloisomerization/Diels–Alder Cascade of 1,5-Bisallenes
Jordi Vila, Miquel Solà, Anna Pla‐Quintana, Anna Roglans
Abstract
The synthesis of spiro compounds featuring seven- and six-membered rings in the spirobicyclic motif is successfully achieved through a cascade process encompassing a rhodium(I)-catalyzed cycloisomerization followed by a highly selective Diels-Alder homodimerization. The scope of the reaction is analyzed based on a series of synthetic substrates, and control experiments and DFT calculations led us to justify the exquisite degree of selectivity observed.
Topics & Concepts
CycloisomerizationCascadeCatalysisDiels–Alder reactionChemistryStereochemistryCombinatorial chemistryOrganic chemistryChromatographyCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms