289471-41-6Relevant academic research and scientific papers
Rhodium-catalyzed hydroformylation of 1-allylpyrrole as an unexpected way to 5,6-dihydroindolizine synthesis
Lazzaroni, Raffaello,Settambolo, Roberta,Caiazzo, Aldo,Pontorno, Lorenzo
, p. 320 - 323 (2000)
When 1-allylpyrrole was subjected to hydroformylation conditions with Rh4(CO)12 as the catalyst precursor, at 120 atm total pressure, at 20 and 100°C, 5,6-dihydroindolizine was found unexpectedly, together with the expected branched aldehyde, the linear isomer being obtained in traces amounts only. An annulation via a nucleophilic attack of the pyrrole C2 carbon atom on the carbonyl group of the linear aldehyde, followed by dehydration of the intermediate alcohol, possibly generates the indolizine structure.
Br?nsted acid-mediated annulations of pyrroles featuring N-tethered α,β-unsaturated ketones and esters: Total syntheses of (±)-tashiromine and (±)-indolizidine 209I
Olivier, Wesley J.,Gardiner, Michael G.,Bissember, Alex C.,Smith, Jason A.
supporting information, p. 5436 - 5441 (2018/05/16)
This study provides the first report of the construction of tetrahydroindolizines and tetrahydropyrrolo[1,2-a]azepines via Br?nsted acid-mediated annulation of pyrroles featuring N-tethered α,β-unsaturated esters. In addition, the Br?nsted acid-catalyzed cyclization of pyrroles featuring pendant α,β-unsaturated ketones was applied to complete total syntheses of the indolizidine alkaloids (±)-tashiromine and (±)-indolizidine 209I.
The influence of chiral auxiliaries and catalysts on the selectivity of intramolecular conjugate additions of pyrrole to N-tethered Michael acceptors
Banwell, Martin G.,Beck, Daniel A.S.,Smith, Jason A.
, p. 157 - 159 (2007/10/03)
A series of pyrroles incorporating N-tethered acrylates and related groups has been prepared and examined for their capacity to undergo intramolecular Michael addition reactions to form, in a diastereo- or enantio-selective fashion, the corresponding 8-substituted tetrahydroindolizidine or homologues thereof.
