HETEROAROMATIC TRAPPING OF TRICYCLIC 2-OXIDOCYCLOPENTENYL CATIONS: A SURPRISINGLY EFFICIENT EXAMPLE OF INTERMOLECULAR INTERRUPTED NAZAROV REACTION

作者：Rieder Curtis J; Fradette Ryan J; West Frederick G^*

来源：Heterocycles, 2010, 80(2): 1413-1427.

DOI：10.3987/COM-09-S(S)132

• Nazarov Reaction
• Domino Process
• Heteroaromatic
• Electrophilic Aromatic Substitution
• Triquinane

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.

• 出版日期2010-3-1