1025469-06-0Relevant articles and documents
Hetero aromatic trapping of tricyclic 2-oxidocyclopentenyl cations: A surprisingly efficient example of intermolecular interrupted nazarov reaction
Rieder, Curtis J.,Fradette, Ryan J.,West, Frederick G.
, p. 1413 - 1427 (2010)
Bis(cycloalkenyl) ketones 2a and 2f underwent Nazarov cyclization and intermolecular trapping by electrophilic aromatic substitution with furans, thiophenes, pyrroles, indoles and dimethoxybenzene. Only the cis-anti-cis diastereomer was isolated with dicyclopentenyl ketone 2a, whereas a mixture of diastereomers was seen with 2f (albeit with complete regioselectivity). Comparable interrupted Nazarov trapping was not seen with acyclic dienones 2b-e, indicating the possible involvement of conformation effects in the polycyclic intermediates derived from 2a and 2f.