93486-60-3Relevant academic research and scientific papers
Cyclopenta[b]annulation of Heteroarenes by Organocatalytic γ′[C(sp3)?H] Functionalization of Ynones
Raghu, Moluguri,Grover, Jagdeep,Ramasastry
, p. 18316 - 18321 (2016)
A new approach for the cyclopenta[b]annulation of heteroarenes through metal-free and directing-group-free γ′[C(sp3)?H] functionalization and intramolecular hydroalkylation of ynones has been developed. In an unprecedented event, nucleophilic addition of an organophosphine to the designed ynones triggers γ′[C(sp3)?H] functionalization, leading to the formation of heteroaryl-based ortho-quinodimethane (oQDM) intermediates that undergo carbocyclization to provide cyclopentannulated heteroarenes in good yields and excellent stereoselectivities. Deuterium-labeling experiments substantiated the proposed reaction mechanism as well as the speculated epimerization.
