289471-41-6Relevant articles and documents
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.
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.
