Investigation of a stereoselective co-mediated rearrangement reaction

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4392-4399

  Carbery, David R ^a   Reignier, Serge ^a   Miller, Neil D ^b   Adams, Hary ^a   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; KETONES; STEREOCHEMISTRY;

REARRANGEMENT REACTIONS;

ETHERS;

COBALT; CYCLOHEXANONE DERIVATIVE; ETHER DERIVATIVE; LEWIS ACID;

ARTICLE; ENANTIOSELECTIVITY; EPIMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038441494     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0300587     Document Type: Article

References (42)

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10. For examples of successful conjugate addition reactions of alkynes to cyclic enones, see: (a) Hansen, R. T.; Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1978, 100, 2244. (b) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (c) Maruoka, K.; Shimada, I.; Imoto, H.; Yamamoto, H. Synlett 1994, 519. (d) Kim, S.; Park, J. H.; Jon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 783. (e) Kim, S.; Park, J. H. Synlett 1995, 163. (f) Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182.
11. For examples of successful conjugate addition reactions of alkynes to cyclic enones, see: (a) Hansen, R. T.; Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1978, 100, 2244. (b) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (c) Maruoka, K.; Shimada, I.; Imoto, H.; Yamamoto, H. Synlett 1994, 519. (d) Kim, S.; Park, J. H.; Jon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 783. (e) Kim, S.; Park, J. H. Synlett 1995, 163. (f) Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182.
12. For examples of successful conjugate addition reactions of alkynes to cyclic enones, see: (a) Hansen, R. T.; Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1978, 100, 2244. (b) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (c) Maruoka, K.; Shimada, I.; Imoto, H.; Yamamoto, H. Synlett 1994, 519. (d) Kim, S.; Park, J. H.; Jon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 783. (e) Kim, S.; Park, J. H. Synlett 1995, 163. (f) Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182.
13. For examples of successful conjugate addition reactions of alkynes to cyclic enones, see: (a) Hansen, R. T.; Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1978, 100, 2244. (b) Schwartz, J.; Carr, D. B.; Hansen, R. T.; Dayrit, F. M. J. Org. Chem. 1980, 45, 3053. (c) Maruoka, K.; Shimada, I.; Imoto, H.; Yamamoto, H. Synlett 1994, 519. (d) Kim, S.; Park, J. H.; Jon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 783. (e) Kim, S.; Park, J. H. Synlett 1995, 163. (f) Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182.
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16. For a related rearrangement reaction which uses oxonium ion stabilization, see: (a) Smith, A. B., III; Verhoest, P. R.; Minbiole, K. P.; Lim, J. J. Org. Lett. 1999, 1, 909. (b) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Beauchamp, T. J. Org. Lett. 1999, 1, 913. (c) For a related O to C rearrangement see: Buffet, M. F.; Dixon, D. J.; Edwards, G. L.; Ley, S. V.; Tate, E. W. J. Chem. Soc., Perkin Trans. 1 2000, 1815. (d) Zhang, Y.; Reynolds, N. T.; Manju, K.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720. (e) Sollogoub, M.; Mallet, J.-M.; Sinay, P. Angew. Chem., Int. Ed. 2000, 39, 362.
17. For a related rearrangement reaction which uses oxonium ion stabilization, see: (a) Smith, A. B., III; Verhoest, P. R.; Minbiole, K. P.; Lim, J. J. Org. Lett. 1999, 1, 909. (b) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Beauchamp, T. J. Org. Lett. 1999, 1, 913. (c) For a related O to C rearrangement see: Buffet, M. F.; Dixon, D. J.; Edwards, G. L.; Ley, S. V.; Tate, E. W. J. Chem. Soc., Perkin Trans. 1 2000, 1815. (d) Zhang, Y.; Reynolds, N. T.; Manju, K.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720. (e) Sollogoub, M.; Mallet, J.-M.; Sinay, P. Angew. Chem., Int. Ed. 2000, 39, 362.
18. For a related rearrangement reaction which uses oxonium ion stabilization, see: (a) Smith, A. B., III; Verhoest, P. R.; Minbiole, K. P.; Lim, J. J. Org. Lett. 1999, 1, 909. (b) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Beauchamp, T. J. Org. Lett. 1999, 1, 913. (c) For a related O to C rearrangement see: Buffet, M. F.; Dixon, D. J.; Edwards, G. L.; Ley, S. V.; Tate, E. W. J. Chem. Soc., Perkin Trans. 1 2000, 1815. (d) Zhang, Y.; Reynolds, N. T.; Manju, K.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720. (e) Sollogoub, M.; Mallet, J.-M.; Sinay, P. Angew. Chem., Int. Ed. 2000, 39, 362.
19. For a related rearrangement reaction which uses oxonium ion stabilization, see: (a) Smith, A. B., III; Verhoest, P. R.; Minbiole, K. P.; Lim, J. J. Org. Lett. 1999, 1, 909. (b) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Beauchamp, T. J. Org. Lett. 1999, 1, 913. (c) For a related O to C rearrangement see: Buffet, M. F.; Dixon, D. J.; Edwards, G. L.; Ley, S. V.; Tate, E. W. J. Chem. Soc., Perkin Trans. 1 2000, 1815. (d) Zhang, Y.; Reynolds, N. T.; Manju, K.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720. (e) Sollogoub, M.; Mallet, J.-M.; Sinay, P. Angew. Chem., Int. Ed. 2000, 39, 362.
20. For a related rearrangement reaction which uses oxonium ion stabilization, see: (a) Smith, A. B., III; Verhoest, P. R.; Minbiole, K. P.; Lim, J. J. Org. Lett. 1999, 1, 909. (b) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Beauchamp, T. J. Org. Lett. 1999, 1, 913. (c) For a related O to C rearrangement see: Buffet, M. F.; Dixon, D. J.; Edwards, G. L.; Ley, S. V.; Tate, E. W. J. Chem. Soc., Perkin Trans. 1 2000, 1815. (d) Zhang, Y.; Reynolds, N. T.; Manju, K.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720. (e) Sollogoub, M.; Mallet, J.-M.; Sinay, P. Angew. Chem., Int. Ed. 2000, 39, 362.
21. For a preliminary report of this work, see: Carbery, D. R.; Reignier, S.; Myatt, J. W.; Miller, N. D.; Harrity, J. P. A. Angew. Chem., Int. Ed. 2002, 41, 2584.
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24. 13C NMR chemical shifts of the carbon β to the ether oxygen: Barillier, D.; Strobel, M. P.; Morin, L.; Paquer, D. Tetrahedron 1983, 39, 767.
25. For a detailed discussion of the dynamic behaviour of Nicholas carbocations as well as their reactivity and stability, see: Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749.
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28. Crystallographic data for trans-20 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 194399. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
29. Taken as an average of the two smaller bisecting angles.
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37. (a) This conformation of 23 is reminiscent of all-trans-1,2,3,4,5,6-hexaisopropylcyclohexane in which all groups are located in the axial position to minimise repulsive steric interactions in the all-equatorial conformation. See: Goren, Z.; Biali, S. E. J. Am. Chem. Soc. 1990, 112, 893.
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39. 1H NMR chemical shift values and coupling constants measured for this compound match closely those observed for 25. Crystallographic data for trans-25 and cis-28 are included in the Supporting Information.
40. 4: Carbery, D. R.; Miller, N. D.; Harrity, J. P. A. Chem. Commun. 2002, 1546.
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42. Enantioselective reduction of ketone 5b (Scheme 2) to the propargylic alcohol was carried out using the method of Midland and co-workers: Midland, M. M.; McDowell, D. C.; Hatch, R. L.; Tramontano, A. J. Am. Chem. Soc. 1980, 102, 867. The enantiomeric purity of the starting complex 11Z could not be determined directly but was measured at the lactone precursor (6b, Scheme 2). The absolute configurations of 11Z and trans-20 have not been determined.