Hetero aromatic trapping of tricyclic 2-oxidocyclopentenyl cations: A surprisingly efficient example of intermolecular interrupted nazarov reaction

Heterocycles

Volumn 80, Issue 2, 2010, Pages 1413-1427

  Rieder, Curtis J ^a   Fradette, Ryan J ^a   West, Frederick G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

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

Indexed keywords

EID: 77955668355     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-09-S(S)132     Document Type: Article

References (30)

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22. Similarly, the indole trapping described by Basak and Tius may be an especially effective process due to a longer lifetime conferred upon the cationic intermediate from additional conjugation.
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26. A structurally similar compound to 9 had been reported, prepared via arylcuprate 1,4-addition to a methylenecyclopentanone: A.B. Smith, B.A. Wexler, and J.S. Slade Tetrahedron Lett. 21 1980 3237
27. Epimers 10j and 11j were distinguished by analysis of the coupling constants for the hydrindan bridgehead proton adjacent to the ketone. For the cis isomer 10j, two small couplings and one large trans-diaxial coupling were observed, while for trans isomer 11j, two large trans-diaxial couplings were observed.
28. See reference 10 for the preparation of 2g.
29. Major product 13 was assigned the indicated relative stereochemical configuration based upon vicinal coupling constants and the observation of several unambiguous rOe correlations in the 2D-TROESY spectrum.
30. Spectral data for 2f, 3a-c, 3j, 8, 10a-c, 11a-c, 10j and 11j are found in the electronic supplementary information accompanying reference 6.