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Paper | Special issue | Vol 80, No. 2, 2010, pp.1413-1427
Published online: 10th November, 2009
DOI: 10.3987/COM-09-S(S)132
Heteroaromatic Trapping of Tricyclic 2-Oxidocyclopentenyl Cations: A Surprisingly Efficient Example of Intermolecular Interrupted Nazarov Reaction

Curtis J. Rieder, Ryan J. Fradette, and Frederick G. West*

*Gunning/Lemieux Chemistry Center, Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada

Abstract

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.

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