Gold-Catalyzed Double Spirocyclization of 3-Ene-1,7-diyne Esters to Dispiroheterocycles
Jichao Chen, Zhen Liu, Andrés Felipe León Rojas, Weidong Rao, Philip Wai Hong Chan
Abstract
A synthetic method to prepare dispiroheterocycles containing two all-carbon quaternary centers efficiently that relies on the gold(I)-catalyzed double spirocyclization of 3-ene-1,7-diyne esters is described. The suggested mechanism delineates a rare example of a dispirocyclization featuring two 1, n -acyloxy shifts comprising a 1,3-acyloxy migration and an interrupted 1,5-acyl migration that was achieved with the assistance of residual water in the reaction media.
Topics & Concepts
ChemistryCatalysisEne reactionCombinatorial chemistryQuaternary carbonMedicinal chemistryStereochemistryOrganic chemistryEnantioselective synthesisCatalytic Alkyne ReactionsSynthetic Organic Chemistry MethodsPhytochemical compounds biological activities