631869-23-3Relevant articles and documents
Palladium-catalyzed N1-selective allylation of indoles with allylic alcohols promoted by titanium tetraisopropoxide
Chang, Chieh-Yu,Lin, Yu-Huan,Wu, Yen-Ku
supporting information, p. 1116 - 1119 (2019/01/29)
The direct N1-selective allylation of indoles with allylic alcohols has been accomplished by synergistic functions of palladium catalysts and titanium tetraisopropoxide. The site selectivity is notably different from that observed in other related transition metal-catalyzed approaches. This chemistry provides a facile route to a variety of allylated indoles in synthetically useful yields. The utility of this simple allylation reaction was demonstrated with the first total synthesis of (+)-N-(4′-hydroxyprenyl)-cyclo(alanyltryptophyl), which was completed in five steps, starting from l-tryptophan methyl ester hydrochloride.
Enantioselective synthesis of polycyclic nitrogen heterocycles by Rh-catalyzed alkene hydroacylation: Constructing six-membered rings in the absence of chelation assistance
Du, Xiang-Wei,Ghosh, Avipsa,Stanley, Levi M.
supporting information, p. 4036 - 4039 (2014/08/18)
Catalytic, enantioselective hydroacylations of N-allylindole-2- carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of
Cooperative catalysis approach to intramolecular hydroacylation
Beletskiy, Evgeny V.,Sudheer,Douglas, Christopher J.
experimental part, p. 5884 - 5893 (2012/09/21)
Prior examples of hydroacylation to form six- and seven-membered ring ketones require either embedded chelating groups or other substrate design strategies to circumvent competitive aldehyde decarbonylation. A cooperative catalysis strategy enabled intram
One pot hydroformylation/intramolecular aldol condensation reactions of 1-allyl-2-carbonylpyrroles: A new entry into hydroindolizines synthesis
Settambolo, Roberta,Miniati, Sandra,Lazzaroni, Raffaello
, p. 2953 - 2961 (2007/10/03)
7-Formyl-5-methyl-5,6-dihydroindolizine and 7-formyl-6-methyl-5,6-dihydroindolizine were obtained via a domino hydroformylation/cyclization/dehydration reactions sequence starting from the corresponding 1-allyl-2-formylpyrroles. An intramolecular aldol condensation between the carbon atom adjacent to the formyl group in the chain of the produced aldehydes and the carbonyl group directly bonded to the pyrrole ring most likely generates the indolizine structure. 7-Formyl-6,8-dimethyl-5,6-dihydroindolizine was similarly synthesized by using 2-acetyl-1-(2-methylprop-2-enyl) pyrrole.
Organoyttrium-catalyzed sequential cyclization/silylation reactions of nitrogen-heteroaromatic dienes demonstrating 'aryl-directed' regioselectivity
Molander, Gary A.,Schmitt, Monika H.
, p. 3767 - 3770 (2007/10/03)
The reaction of 1-allyl-2-vinyl-1H-pyrroles and 1-allyl-2-vinyl-1H- indoles with arylsilanes in the presence of catalytic [Cp(TMS)2Y(μ-Me)]2 leads to highly selective cyclization/silylation events. In this process the active catalyst for the reaction, 'Cp(TMS)2YH', undergoes initial olefin insertion at the vinyl group. Even isopropenyl substituents on the heteroaromatics react in preference to less sterically encumbered allyl groups. Furthermore, the observed regioselectivity reflects an 'aryl- directed' process, whereby the more highly substituted secondary or tertiary organometallic is initially generated. This intermediate undergoes cyclization onto the remaining alkene and subsequent silylation by a σ-bond metathesis reaction, affording the observed products.
