Ammonium ylide versus carbonyl ylide formation in the Rhodium(II)-catalyzed decomposition of diazoacetylureas. Generation and X-ray structure of a stable five-membered N-acyl ammonium ylide

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3323-3326

  Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; IMIDAZOLE DERIVATIVE; OXAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030907664     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00618-7     Document Type: Article

References (30)

1. Doyle, M. P. Chem. Rev. 1986, 86, 919. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford; Vol. 12, 1995, p 387. Taber. T. F. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 3, 1990, p 1045. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
2. Doyle, M. P. Chem. Rev. 1986, 86, 919. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford; Vol. 12, 1995, p 387. Taber. T. F. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 3, 1990, p 1045. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
3. Doyle, M. P. Chem. Rev. 1986, 86, 919. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford; Vol. 12, 1995, p 387. Taber. T. F. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 3, 1990, p 1045. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
4. Doyle, M. P. Chem. Rev. 1986, 86, 919. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford; Vol. 12, 1995, p 387. Taber. T. F. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 3, 1990, p 1045. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
5. Doyle, M. P. Chem. Rev. 1986, 86, 919. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. Doyle, M. P. Comprehensive Organometallic Chemistry II; Hegedus, L., Ed.; Pergamon Press: Oxford; Vol. 12, 1995, p 387. Taber. T. F. Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford; Vol. 3, 1990, p 1045. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
6. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
7. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
8. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
9. Doyle, M. P.; Recl. Trav. Chim. Pays-Bas 1991, 110, 305 Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
10. Doyle, M. P.; Recl. Trav. Chim. Pays-Bas 1991, 110, 305 Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
11. For reviews on the chemistry of isomünchnones, see: Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123. Newton, C. G.; Ramsden, C. A. Tetrahedron 1982, 38, 2965. Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1.
12. For reviews on the chemistry of isomünchnones, see: Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123. Newton, C. G.; Ramsden, C. A. Tetrahedron 1982, 38, 2965. Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1.
13. For reviews on the chemistry of isomünchnones, see: Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123. Newton, C. G.; Ramsden, C. A. Tetrahedron 1982, 38, 2965. Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1.
14. For some recent examples, see: Padwa, A.; Austin, D. J.; Price, A. T.; Weingarten, M. D. Tetrahedron 1996, 52, 3247. Prein, M.; Padwa, A. Tetrahedron Lett. 1996, 37, 6981. Marino, J. P. Jr.; Osterhout, M. H.; Padwa, A. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P. Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518
15. For some recent examples, see: Padwa, A.; Austin, D. J.; Price, A. T.; Weingarten, M. D. Tetrahedron 1996, 52, 3247. Prein, M.; Padwa, A. Tetrahedron Lett. 1996, 37, 6981. Marino, J. P. Jr.; Osterhout, M. H.; Padwa, A. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P. Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518
16. For some recent examples, see: Padwa, A.; Austin, D. J.; Price, A. T.; Weingarten, M. D. Tetrahedron 1996, 52, 3247. Prein, M.; Padwa, A. Tetrahedron Lett. 1996, 37, 6981. Marino, J. P. Jr.; Osterhout, M. H.; Padwa, A. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P. Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518
17. For some recent examples, see: Padwa, A.; Austin, D. J.; Price, A. T.; Weingarten, M. D. Tetrahedron 1996, 52, 3247. Prein, M.; Padwa, A. Tetrahedron Lett. 1996, 37, 6981. Marino, J. P. Jr.; Osterhout, M. H.; Padwa, A. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P. Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518
18. For some recent examples, see: Padwa, A.; Austin, D. J.; Price, A. T.; Weingarten, M. D. Tetrahedron 1996, 52, 3247. Prein, M.; Padwa, A. Tetrahedron Lett. 1996, 37, 6981. Marino, J. P. Jr.; Osterhout, M. H.; Padwa, A. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P. Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518
19. Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418.
20. Taber, D. F.; Ruckle, R. E. Jr.; Hennesy, M. J. Org. Chem. 1986, 51, 4077.
21. All new compounds in this study were fully characterized (IR, NMR, elemental analysis).
22. The formation of azines in the rhodium-catalyzed decomposition of diazo ketones is not without precedent: Fernández Mateos, A.; Pascual Coca, G.; Pérez Alonso, J. J.; Rubio González, R.; Tapia Hernández, C. Synlett 1996, 1134.
23. Crystallographic data for structures 6 and 9 have been deposited at the Cambridge Crystallographic Data Center. The coordinates can be obtained on request from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
24. Doyle, M. P. Comprehensive Organometallic Chemistry II, Hegedus, L., Ed.; Pergamon Press: Oxford; Vol. 12, 1995, p. 421, see in particular p. 431.
25. For reviews on ammonium ylides, see: Johnson, A. W. Ylide Chemistry, Academic Press: New York, 1966. Zugravescu I.; Petrovanu, M. N-Ylide Chemistry, MacGraw-Hill: New York, 1976 Claus, P. in Houben-Weyl, Vol. E14b; Klaman, D.; Hageman, H.; Eds; Thieme: Stuttgart, 1990, p. 210; and refs 1,2, and 11.
26. For reviews on ammonium ylides, see: Johnson, A. W. Ylide Chemistry, Academic Press: New York, 1966. Zugravescu I.; Petrovanu, M. N-Ylide Chemistry, MacGraw-Hill: New York, 1976 Claus, P. in Houben-Weyl, Vol. E14b; Klaman, D.; Hageman, H.; Eds; Thieme: Stuttgart, 1990, p. 210; and refs 1,2, and 11.
27. For reviews on ammonium ylides, see: Johnson, A. W. Ylide Chemistry, Academic Press: New York, 1966. Zugravescu I.; Petrovanu, M. N-Ylide Chemistry, MacGraw-Hill: New York, 1976 Claus, P. in Houben-Weyl, Vol. E14b; Klaman, D.; Hageman, H.; Eds; Thieme: Stuttgart, 1990, p. 210; and refs 1,2, and 11.
28. Kappe, C. O.; Roschger, P. J. Heterocycl. Chem. 1989, 26, 55.
29. 2,5-Bis-aryl isomünchnones have also been reported to be stable in the open air for weeks; see: Hamaguchi, M.; Ibata, T. Tetrahedron Lett. 1974, 4475. For a previous example of an aminoisomünchnone proposed as a transient intermediate, see: Doyle, M. P.; Pieters, R. J.; Taunton, J.; Pho, H. Q.; Padwa, A.; Hertzog, D. L.; Precedo, L. J. Org. Chem. 1991, 56, 820.
30. 2,5-Bis-aryl isomünchnones have also been reported to be stable in the open air for weeks; see: Hamaguchi, M.; Ibata, T. Tetrahedron Lett. 1974, 4475. For a previous example of an aminoisomünchnone proposed as a transient intermediate, see: Doyle, M. P.; Pieters, R. J.; Taunton, J.; Pho, H. Q.; Padwa, A.; Hertzog, D. L.; Precedo, L. J. Org. Chem. 1991, 56, 820.