Tandem oxy-Cope/transannular ene reaction of 1,2-divinylcyclohexanols

Organic Letters

Volumn 2, Issue 5, 2000, Pages 663-665

  Warrington, Jeffrey M ^a   Yap, Glenn P A ^a   Barriault, Louis ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000684358     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005502w     Document Type: Article

References (17)

1. (a) Ho, T.-L. Tandem Organic reacrions; Wiley: New York, 1992.
2. (b) Ziegler, F. In Comprehensive Organic Synthesis, Combining C-C π bond; Paquette, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5; Chapter 7.3.
3. (c) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
4. Chorlton, A. P.; Morris, G. A.; Sutherland, J. K. J. Chem. Soc., Perkin Trans. 1 1991, 1205.
5. Paquette, L. A.; Nakatani, S.; Zydowsky, T. M.; Edmondson, S. D.; Sun, Q.-L.; Skerlj, R. J. Org. Chem. 1999, 64, 3244.
6. Rajagopalan, K.; Janardhanam, S.; Balakumar, A. J. Org. Chem. 1993, 58, 5482 and references therein.
7. Linstrumelle, G.; Derguini-Boumechal, F.; Huynh, C. Tetrahedron Lett. 1979, 20, 1503.
8. Swern, D.; Mancuso, A. J. Synthesis 1981, 165.
9. Paquette, L. A.; Pegg, N. A.; Toops, D.; Maynard, G. D.; Rogers, R. D. J. Am. Chem. Soc. 1990, 112, 111.
10. Smith, A. B., III.; Branca, S. J.; Pilla, N. N.; Guaciaro, M. A. J. Org. Chem. 1982, 47, 1855.
11. Boeckman, R. K., Jr.; Bruza, K. J. Tetrahedron Lett. 1977, 18, 4187.
12. Holt, D. A. Tetrahedron Lett. 1981, 22, 2243.
13. Typical procedure: A solution of 13 (24 mg, 0.12 mmol) in dry toluene (5 mL) was heated in a pressure tube (previously washed with aqueous 2-propanol/NaOH solution, water, and acetone) for 5 h at 220 °C. The tube was cooled to room temperature, and the solution was transferred and concentrated. The residue was purified by flash chromatography (10% ether in hexanes) to give 22 as a colorless oil (20 mg, 83%).
14. Barriault, L. Unpublished results.
15. Recently, Paquette et al. reported that alkoxy substituents on the olefin have a deceleration rate effect on the anionic oxy-Cope rearrangement. See: Haeffner, F.; Houk, K. N.; Reddy, R. Y.; Paquette, L. A. J. Am. Chem. Soc., in press.
16. Kato, T.; Tsunakawa, M.; Sasaki, N.; Aizawa, H.; Fujita, K.; Kitahara, Y.; Takahashi, N. Phytochemistry 1977, 16, 45.
17. Birch, A. J.; Richards, R. W.; Smith, H.; Harris, A.; Whalley, W. B. Tetrahedron 1959, 7, 241.