An anionic C3-C5 ring expansion of β-ketocyclopropanes to cyclopentenols

Organic Letters

Volumn 4, Issue 2, 2002, Pages 221-224

  Greatrex, Ben W ^a   Taylor, Dennis K ^a   Tiekink, Edward R T ^b  

^a UNIVERSITY OF ADELAIDE   (Australia)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

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ARTICLE;

EID: 0008936422     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010246o     Document Type: Article

References (23)

1. 5 ring expansion, see: (a) Salaun, J. Rearrangements involving the cyclopropyl group. In The Chemistry of the cyclopropyl group; Patai, S.Z. R., Ed.; Wiley: Toronto, 1987. (b) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon, Oxford, 1991; Vol. 5, 8.1, p 899. (c) Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1985, 33, 247 and references therein.
2. 5 ring expansion, see: (a) Salaun, J. Rearrangements involving the cyclopropyl group. In The Chemistry of the cyclopropyl group; Patai, S.Z. R., Ed.; Wiley: Toronto, 1987. (b) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon, Oxford, 1991; Vol. 5, 8.1, p 899. (c) Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1985, 33, 247 and references therein.
3. 5 ring expansion, see: (a) Salaun, J. Rearrangements involving the cyclopropyl group. In The Chemistry of the cyclopropyl group; Patai, S.Z. R., Ed.; Wiley: Toronto, 1987. (b) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon, Oxford, 1991; Vol. 5, 8.1, p 899. (c) Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1985, 33, 247 and references therein.
4. Danheiser, R. L.; Martinez-Davila, C.; Morin, J. M. J. Org. Chem. 1980, 45, 1340-1341. Danheiser, R. L.; Bronson, J. L.; Okano, K. J. Am. Chem. Soc. 1985, 107, 4579-4581.
5. Danheiser, R. L.; Martinez-Davila, C.; Morin, J. M. J. Org. Chem. 1980, 45, 1340-1341. Danheiser, R. L.; Bronson, J. L.; Okano, K. J. Am. Chem. Soc. 1985, 107, 4579-4581.
6. Jorgensen, M. J.; Heathcock, C. H. J. Am. Chem. Soc. 1965, 87, 5264.
7. Avery, T. A.; Haselgrove, T. D.; Rathbone, T. J.; Taylor, D. K.; Tiekink, E. R. T. J. Chem. Soc., Chem. Commun. 1998, 333. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546.
8. Avery, T. A.; Haselgrove, T. D.; Rathbone, T. J.; Taylor, D. K.; Tiekink, E. R. T. J. Chem. Soc., Chem. Commun. 1998, 333. Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531-5546.
9. Avery, T. D.; Greatrex, B. W.; Taylor, D. K.; Tiekink, E. R. T. J. Chem. Soc., Perkin Trans, 1, 2000, 1319-1321. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966.
10. Avery, T. D.; Greatrex, B. W.; Taylor, D. K.; Tiekink, E. R. T. J. Chem. Soc., Perkin Trans, 1, 2000, 1319-1321. Avery, T. D.; Fallon, G.; Greatrex, B. W.; Pyke, S. M.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2001, 66, 7955-7966.
11. Avery, T. D.; Jenkins, N. F.; Kimber, M. C.; Lupton, D.; Taylor, D. K. Submitted.
12. Heathcock, C. H.; Buse, C. T.; Kleschick, M. C.; Pirrung, M. C. Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066-1081.
13. Greatrex, B. W.; Taylor, D. K.; Tiekink, E. R. T. Submitted.
14. If the reaction occurred in a concerted manner, then an inversion of relative stereochemistry at Cl and C5 would be expected in the product cyclopentenol.
15. Calculations were performed at the AM1 level of theory using the Spartan suite of programs. Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92715.
16. Denmark, S. E.; Henke, B. R. J. Am. Chem. Soc. 1990, 113, 2177-94 and references therein.
17. Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 2871-2874. Buchert, M.; Reissig, H. Liebigs Ann. 1996, 2007-2013.
18. Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 2871-2874. Buchert, M.; Reissig, H. Liebigs Ann. 1996, 2007-2013.
19. Larsen, S. D. J. Am. Chem. Soc. 1988, 110, 5932. Larsen, S. D.; Fisher, P. V.; Libby, B. E.; Jensen, R. M.; Mizsak, S. A.; Watt, W.; Ronk, W. R.; Hill, S. T. J. Org. Chem. 1996, 61, 4725-4738.
20. Larsen, S. D. J. Am. Chem. Soc. 1988, 110, 5932. Larsen, S. D.; Fisher, P. V.; Libby, B. E.; Jensen, R. M.; Mizsak, S. A.; Watt, W.; Ronk, W. R.; Hill, S. T. J. Org. Chem. 1996, 61, 4725-4738.
21. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570-2572.
22. Ireland, R. E.; Willard, A. K. Tetrahedron Lett. 1975, 3975-3978. Ireland, R. E.; Muellar, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.
23. Ireland, R. E.; Willard, A. K. Tetrahedron Lett. 1975, 3975-3978. Ireland, R. E.; Muellar, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.