A convenient method for the preparation of (Z)-αβ-unsaturated carbonyl compounds

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2908-2910

  Taber, Douglass F ^a   Herr, R Jason ^a   Pack, Shawn K ^a   Geremia, John M ^a  

^a UNIVERSITY OF DELAWARE   (United States)

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EID: 0001031980     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. (a) Kelly, S. E. In Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 1, p 729.
2. (b) Boyd, G. V. In The Chemistry of Enones; John Wiley & Sons: New York, 1989; Pt. 1, p 281.
3. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
4. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
5. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
6. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
7. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
8. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
9. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
10. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
11. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
12. For some general routes to αβ-unsaturated esters and ketones, see: (a) Addition/elimination reactions with selemum derivatives: (i) Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137. (ii) Reich, H. J.; Wollowitz, S. In Organic Reactions, John Wiley & Sons: New York, 1993; Vol 44, p 1. (iii) Hooz, J.; Oudenes, J. Synth. Commun. 1080,10, 667. (b) Addition/elimination reactions with sulfur derivatives: (i) Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. (ii) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976,98. 4887. (iii) Resek, J. E.; Meyers, A. L. Tetrahedron Lett, 1995, 36, 7051. (c) Condensation reactions with stabilized phosphonium ylides (review article,): Maryanoff, B. E., Reitz, A. B. Chem. Rev. 1989, 89, 863. (d) The Horner-Wadsworth-Emmons reaction (review article): see ref 2a. (e) Carbonylations of vmylic halides: Urata, H.; Maekawa, H.; Shigeharu. T.; Fuchikami, T. J. Org. Chem. 1991, 56, 4320. (f) Carbonylations of vinylmercurials: Larock, R. C.; Narayanan, K. J. Org. Chem. 1984, 49, 3411.
13. For (Z)-stereoselective syntheses of α,β-unsaturated esters: (a) With bis(trifluoroethyl)phosphonoesters: Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405. (b) With trimethylphosphonium-propionates: Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979,101, 260. (c) With bis(phenyl) phosphonoesters: Ando, K. Tetrahedron Lett. 1995, 36, 4105. For (Z)-stereoselective syntheses of α,β-unsaturated ketones with stabilized ylides: (d) Pietrusiewicz, K. M.; Monkiewicz, J. Tetrahedron Lett. 1986, 27, 739. (e) Moorhoff, C. M.; Schneider. D. F. Tetrahedron Lett. 1987.28, 4721. (f) McKenna, E. G.; Walker, B. J. J. Chem. Soc., Chem. Commun. 1989, 568.
14. For (Z)-stereoselective syntheses of α,β-unsaturated esters: (a) With bis(trifluoroethyl)phosphonoesters: Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405. (b) With trimethylphosphonium-propionates: Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979,101, 260. (c) With bis(phenyl) phosphonoesters: Ando, K. Tetrahedron Lett. 1995, 36, 4105. For (Z)-stereoselective syntheses of α,β-unsaturated ketones with stabilized ylides: (d) Pietrusiewicz, K. M.; Monkiewicz, J. Tetrahedron Lett. 1986, 27, 739. (e) Moorhoff, C. M.; Schneider. D. F. Tetrahedron Lett. 1987.28, 4721. (f) McKenna, E. G.; Walker, B. J. J. Chem. Soc., Chem. Commun. 1989, 568.
15. For (Z)-stereoselective syntheses of α,β-unsaturated esters: (a) With bis(trifluoroethyl)phosphonoesters: Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405. (b) With trimethylphosphonium-propionates: Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979,101, 260. (c) With bis(phenyl) phosphonoesters: Ando, K. Tetrahedron Lett. 1995, 36, 4105. For (Z)-stereoselective syntheses of α,β-unsaturated ketones with stabilized ylides: (d) Pietrusiewicz, K. M.; Monkiewicz, J. Tetrahedron Lett. 1986, 27, 739. (e) Moorhoff, C. M.; Schneider. D. F. Tetrahedron Lett. 1987.28, 4721. (f) McKenna, E. G.; Walker, B. J. J. Chem. Soc., Chem. Commun. 1989, 568.
16. For (Z)-stereoselective syntheses of α,β-unsaturated esters: (a) With bis(trifluoroethyl)phosphonoesters: Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405. (b) With trimethylphosphonium-propionates: Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979,101, 260. (c) With bis(phenyl) phosphonoesters: Ando, K. Tetrahedron Lett. 1995, 36, 4105. For (Z)-stereoselective syntheses of α,β-unsaturated ketones with stabilized ylides: (d) Pietrusiewicz, K. M.; Monkiewicz, J. Tetrahedron Lett. 1986, 27, 739. (e) Moorhoff, C. M.; Schneider. D. F. Tetrahedron Lett. 1987.28, 4721. (f) McKenna, E. G.; Walker, B. J. J. Chem. Soc., Chem. Commun. 1989, 568.
17. For (Z)-stereoselective syntheses of α,β-unsaturated esters: (a) With bis(trifluoroethyl)phosphonoesters: Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405. (b) With trimethylphosphonium-propionates: Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979,101, 260. (c) With bis(phenyl) phosphonoesters: Ando, K. Tetrahedron Lett. 1995, 36, 4105. For (Z)-stereoselective syntheses of α,β-unsaturated ketones with stabilized ylides: (d) Pietrusiewicz, K. M.; Monkiewicz, J. Tetrahedron Lett. 1986, 27, 739. (e) Moorhoff, C. M.; Schneider. D. F. Tetrahedron Lett. 1987.28, 4721. (f) McKenna, E. G.; Walker, B. J. J. Chem. Soc., Chem. Commun. 1989, 568.
18. For (Z)-stereoselective syntheses of α,β-unsaturated esters: (a) With bis(trifluoroethyl)phosphonoesters: Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405. (b) With trimethylphosphonium-propionates: Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979,101, 260. (c) With bis(phenyl) phosphonoesters: Ando, K. Tetrahedron Lett. 1995, 36, 4105. For (Z)-stereoselective syntheses of α,β-unsaturated ketones with stabilized ylides: (d) Pietrusiewicz, K. M.; Monkiewicz, J. Tetrahedron Lett. 1986, 27, 739. (e) Moorhoff, C. M.; Schneider. D. F. Tetrahedron Lett. 1987.28, 4721. (f) McKenna, E. G.; Walker, B. J. J. Chem. Soc., Chem. Commun. 1989, 568.
19. Ikota, N.; Takamura, N.; Young, S. D.; Ganem, B. Tetrahedron Lett. 1981, 22, 4163.
20. β-Hydride elimination has been shown to be competetive with rhodium-catalyzed 1,5-insertion reactions: (a) Taber, D. F.: Hennessy, M. J.; Louey, J. P. J. Org. Chem. 1992, 57, 436. (b) Hennessy, M. J. Ph.D. Dissertation, The University of Delaware, 1989. (c) Galeazzi, E.; Guzman, A.; Pinedo, A.; Saldana, A.; Torre, D.; Muchowski, J. M. Can. J Chem. 1983, 67, 454.
21. β-Hydride elimination has been shown to be competetive with rhodium-catalyzed 1,5-insertion reactions: (a) Taber, D. F.: Hennessy, M. J.; Louey, J. P. J. Org. Chem. 1992, 57, 436. (b) Hennessy, M. J. Ph.D. Dissertation, The University of Delaware, 1989. (c) Galeazzi, E.; Guzman, A.; Pinedo, A.; Saldana, A.; Torre, D.; Muchowski, J. M. Can. J Chem. 1983, 67, 454.
22. β-Hydride elimination has been shown to be competetive with rhodium-catalyzed 1,5-insertion reactions: (a) Taber, D. F.: Hennessy, M. J.; Louey, J. P. J. Org. Chem. 1992, 57, 436. (b) Hennessy, M. J. Ph.D. Dissertation, The University of Delaware, 1989. (c) Galeazzi, E.; Guzman, A.; Pinedo, A.; Saldana, A.; Torre, D.; Muchowski, J. M. Can. J Chem. 1983, 67, 454.
23. (a) A rhodium(II) acetate-catalyzed method for the elimination of α-diazo β-methoxy ketones to (E)-β-methoxy enones has also been reported: Hudlicky, T.; Olivo, H. F.; Natchus, M. G.; Umpierrez, E. F.; Pandolfi, E.; Volonterio, C. J. Org. Chem. 1990, 55, 4767.
24. 3-promoted decomposition of acyldiazoethanes can be used to prepare enones: Duggleby, P. McC.; Holt, G.; Hope, M. A.; Lewis, A. J. Chem. Soc., Perkin Trans. 1 1972, 3020.
25. (a) Taber, D. F.; Ruckle, R E., Jr.; Hennessy, M. J. J. Org. Chem. 1986, 51, 4077.
26. (b) Taber, D. F.; You, K.; Song, Y. J. Org. Chem. 1995, 60, 1093-
27. (c) Taber, D. F.; Gleave, D. M.; Herr, R. J.; Moody, K.; Hennessy, M. J. J. Org. Chem. 1995, 60, 2283.
28. However, subjection of the α-diazo ester i to the same conditions resulted in exclusive C-C insertion product ii. equation presented
29. 13C NMR spectroscopy, showing no trace of the (E)-isomer in the crude product mixture before chromatography. Early reactions run at higher temperatures showed significant contamination by the (E)-isomer.
30. For a summary of general experimental procedures see: Taber, D. F.; Houze, J. B. J. Org. Chem. 1994, 59. 4004.