123332-18-3Relevant articles and documents
Copper-Catalyzed Enantioselective Domino Arylation/Semipinacol Rearrangement of Allylic Alcohols with Diaryliodonium Salts
Wu, Hua,Wang, Qian,Zhu, Jieping
, p. 13037 - 13041 (2017)
A copper-catalyzed enantioselective arylative semipinacol rearrangement of allylic alcohols was developed. In the presence of a catalytic amount of an in situ generated chiral copper-bisoxazoline complex, reaction of allylic alcohols with diaryliodonium salts afforded spirocycloalkanones in high yields with high diastereo- and enantioselectivities. A two-point binding model engaging the carbon–carbon double bond and the proximal hydroxyl group was proposed to be responsible for the highly efficient chirality transfer.
Photochemical generation and reversible cycloaromatization of a nine-membered ring cyclic enediyne
Pandithavidana, Dinesh R.,Poloukhtine, Andrei,Popik, Vladimir V.
experimental part, p. 351 - 356 (2009/06/18)
Irradiation of the nine-membered ring enediyne precursor, which has one of its triple bonds masked as cyclopropenone, efficiently(φ = 0.34) generates the reactive 4,5-benzocyclonona-2,6-diynol. The latter rapidly equilibrates with the corresponding 1,4-didehydronaphthalene diradical and then undergoes rate- limiting hydrogen abstraction to produce the ultimate product of the Bergman cyclization, benz[f]indanol.
