Ruthenium-catalyzed intramolecular homo-diels - Alder reaction of alkyne-tethered norbornadienes. An entry to fused angular triquinanes

Organic Letters

Volumn 9, Issue 18, 2007, Pages 3607-3610

  Tenaglia, Alphonse ^a   Gaillard, Sylvain ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

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Indexed keywords

EID: 34548525475     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701463r     Document Type: Article

References (28)

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3. (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
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5. Recent examples: (a) [2 + 1]: Bigeault, J.; Giordano, L.; Buono, G. Angew. Chem., Int. Ed. 2005, 44, 4753-4757.
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9. Tenaglia, A.; Giordano, L. Tetrahedron Lett. 2004, 45, 171-174.
10. The first intramolecular HDA reaction between norbornadiene and alkynes using a cobalt catalyst was reported by Lautens. See: (a) Lautens, M.; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9.
11. (b) Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Crudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863-6879.
12. See the Supporting Information.
13. Robinson, S. D.; Wilkinson, G. J. Chem. Soc. 1966, 300-301. nbd = norbornadiene.
14. The pentacyclic structure of the cycloadducts was further confirmed with a single-crystal X-ray analysis of the dinitrile 2d. CCDC-650416 contains the supplementary crystallographic data. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (int.) +44-1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk]. See also the Supporting Information.
15. Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-173.
16. This unexpected etherification is currently being investigated in our laboratories.
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23. Nickon, A.; Kwasnik, H. R.; Mathew, C. T.; Swartz, T. D.; Williams, R. O.; DiGiorgio, J. B. J. Org. Chem. 1978, 43, 3904-3916.
24. (a) Heumann, A.; Kaldy, S.; Tenaglia, A. J. Chem. Soc., Chem. Commun. 1993, 420-422.
25. (b) Heumann, A.; Kaldy, S.; Tenaglia, A. Tetrahedron 1994, 50, 539-558.
26. Lautens suggested the selective cleavage of two carbon-carbon bonds of the cyclopropane unit as a route to functionalized linearly or angularly fused triquinanes but achievement of this strategy was only demonstrated to the bicyclic structure (diquinanes). See: (a) Lautens, M.; Tam, W.; Blackwell, J. J. Am. Chem. Soc. 1997, 119, 623-624.
27. (b) Lautens, M.; Blackwell, J. Synthesis 1998, 537-546. Our strategy is complementary and based on the cleavage of one cyclopropane bond and one adjacent carbon-carbon bond, see below: It should be noted that the diquinanes obtained by Lautens required an alkoxy substituent on the methano bridge of deltacyclanes to achieve regiochemistry and used an environmentally unfriendly stoichiometrical oxymercuriation step for cleavage of the cyclopropane.
28. CCDC-650417 contains the supplementary crystallographic data. See the Supporting Information for details.