Gold-Catalyzed Domino Cycloisomerization/Alkoxylation: An Entry to 3,4-Dihydro-1<i>H</i>-[1,4]oxazino[4,3-<i>a</i>]indole
Aurélien Dupeux, Véronique Michelet
Abstract
A novel and mild synthetic route for the preparation of functionalized polycyclic indole skeletons via a gold-mediated cycloisomerization/alkoxylation of 1,6-aldehyde-yne has been developed. This atom-economical catalytic process that associates IPrAu(MeCN)BF4 and an alcohol demonstrated remarkable selectivity in accessing functionalized 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indole derivatives of high synthetic utility (21 examples, yields of ≤96%) and could be optimized under asymmetric conditions with an enantiomeric excess of ≤86%.
Topics & Concepts
CycloisomerizationChemistryIndole testDominoCatalysisAldehydeEnantiomerAlcoholSelectivityCombinatorial chemistryCascade reactionMedicinal chemistryOrganic chemistryStereochemistryCatalytic Alkyne ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods