Oxy-Cope rearrangements of bicyclo[3.2.0]heptenones. Synthesis of bicyclo[4.2.1]non-1(4)-en-6-ones and bicyclo[5.2.1]dec-1(10)-en-5-ones

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3379-3386

  Verma, Sharad K ^a   Nguyen, Que H ^a   MacDougall, James M ^a   Fleischer, Everly B ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.2.0]HEPTANE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS;

BICYCLO COMPOUNDS; INDICATORS AND REAGENTS; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOSILICON COMPOUNDS;

EID: 0034595945     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991765w     Document Type: Article

References (20)

1. For a recent review of the synthesis and reactions of cyclobuten-ones, see: Moore, H. W.; Yerxa, B. R. Adv. Strain Org. Chem. 1995, 4, 81-162.
2. Gayo, L. G.; Winters, M. P.; Moore, H. W. J. Org. Chem. 1992, 57, 6896.
3. For examples see the following and references therein: (a) Santora, V. S.; Moore, H. W. J. Org. Chem. 1996, 61, 7976. (b) Santora, V. S.; Moore, H. W. J. Am. Chem. Soc. 1995, 117, 8486. (c) Jung, M. E.; Rayle, H. L. J. Org. Chem. 1997, 62, 4601. (d) Enholm, E. J.; Zia, Z. Z. J. J. Org. Chem. 1997, 62, 174.
4. For examples see the following and references therein: (a) Santora, V. S.; Moore, H. W. J. Org. Chem. 1996, 61, 7976. (b) Santora, V. S.; Moore, H. W. J. Am. Chem. Soc. 1995, 117, 8486. (c) Jung, M. E.; Rayle, H. L. J. Org. Chem. 1997, 62, 4601. (d) Enholm, E. J.; Zia, Z. Z. J. J. Org. Chem. 1997, 62, 174.
5. For examples see the following and references therein: (a) Santora, V. S.; Moore, H. W. J. Org. Chem. 1996, 61, 7976. (b) Santora, V. S.; Moore, H. W. J. Am. Chem. Soc. 1995, 117, 8486. (c) Jung, M. E.; Rayle, H. L. J. Org. Chem. 1997, 62, 4601. (d) Enholm, E. J.; Zia, Z. Z. J. J. Org. Chem. 1997, 62, 174.
6. For examples see the following and references therein: (a) Santora, V. S.; Moore, H. W. J. Org. Chem. 1996, 61, 7976. (b) Santora, V. S.; Moore, H. W. J. Am. Chem. Soc. 1995, 117, 8486. (c) Jung, M. E.; Rayle, H. L. J. Org. Chem. 1997, 62, 4601. (d) Enholm, E. J.; Zia, Z. Z. J. J. Org. Chem. 1997, 62, 174.
7. For reviews of the oxy-Cope rearrangement, see: (a) Paquette, L. A. Tetrahedron 1997, 53, 13971-14020. (b) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609-626. (c) Lutz, R. P. Chem. Rev. 1984, 84, 6-243.
8. For reviews of the oxy-Cope rearrangement, see: (a) Paquette, L. A. Tetrahedron 1997, 53, 13971-14020. (b) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609-626. (c) Lutz, R. P. Chem. Rev. 1984, 84, 6-243.
9. For reviews of the oxy-Cope rearrangement, see: (a) Paquette, L. A. Tetrahedron 1997, 53, 13971-14020. (b) Paquette, L. A. Angew. Chem., Int. Ed. Engl. 1990, 29, 609-626. (c) Lutz, R. P. Chem. Rev. 1984, 84, 6-243.
10. (a) MacDougall, J. M.; Turnbull, P. S.; Verma, S. K.; Moore, H. W. J. Org. Chem. 1997, 62, 3792.
11. (b) MacDougall, J. M.; Santora, V. J.; Verma, S. K.; Turnbull, P.; Hernandez, C. R.; Moore, H. W. J. Org. Chem. 1998, 63, 6905.
12. Satyanarayana, N.; Nayak, U. K. Synth. Commun. 1985, 15, 331.
13. For a review of strained bridgehead alkenes, see: Warner, P. M. Chem. Rev. 1989, 89, 1067.
14. Wijsman, G. W.; de Wolf, W. H.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L., J. Am. Chem. Soc. 1992, 114, 9191.
15. For a review concerning the X-ray data of bridged alkenes, see: Lease, T. G.; Shea, K. J. Advances in Theoretically Interesting Molecules; JAI Press Inc.: New York, 1992; Vol. 2, pp 79-112.
16. Ermer, O.; Lifson, S. J. Am. Chem. Soc. 1973, 95, 4121.
17. Liu, H.; Tomooka, C.; Moore, H. W. Synth. Commun. 1997, 27, 2177.
18. For the preparation of TBSOTf, see: Corey, E. J. et. al. Tetrahedron Lett. 1981, 3465.
19. For related 1.6-additions of cuprates, see: Liu, H.; Tomooka, C.; Moore, H. W. J. Org. Chem. 1996, 61, 6009.
20. For a preparation of vinyllithium, see: Seyfurth, D.; Wiener, M. A. J. Am. Chem. Soc. 1961, 83, 3583.