Unusually reactive and selective carbonyl ylides for three-component cycloaddition reactions

Journal of the American Chemical Society

Volumn 131, Issue 3, 2009, Pages 1101-1105

  Deangelis, Andrew ^a   Taylor, Michael T ^a   Fox, Joseph M ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; CYCLOADDITION REACTION; DIASTEREO-SELECTIVITY; ETHYL DIAZOACETATE; FUNCTIONALIZED; TETRA-HYDROFURAN; THREE COMPONENT REACTIONS; THREE-COMPONENT; TRANSITION STATE;

ALDEHYDES; ALKYLATION; CYCLOADDITION; RHODIUM;

CARBONYLATION;

4 FLUOROBENZALDEHYDE; ALDEHYDE; ALPHA DIAZOESTER DERIVATIVE; CARBONYL DERIVATIVE; CARBONYL YLIDE DERIVATIVE; DIAZOACETIC ACID ETHYL ESTER; ESTER DERIVATIVE; UNCLASSIFIED DRUG; CARBONIC ACID; REACTIVE OXYGEN METABOLITE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY; X RAY DIFFRACTION; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM;

CARBONIC ACID; CYCLIZATION; MOLECULAR STRUCTURE; REACTIVE OXYGEN SPECIES; STEREOISOMERISM;

EID: 61749089151     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807184r     Document Type: Article

References (40)

1. (a) Gothelf, K. V.; Jø rgensen, K. A. Chem. Rev. 1998, 98, 863.
2. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
3. (c) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley: New York, 1998. (d) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765.
4. (e) Mehta, G.; Muthusamy, S. Tetrahedron 2002, 58, 9477.
5. (2)(a) Padwa, A.; Dean, D. C.; Osterhout, M. H.; Precedo, L.; Semones, M. A. J. Org. Chem. 1994, 59, 5347.
6. (b) Kitagaki, S.; Anada, M.; Kataoka, O.; Matsuno, K.; Umeda, C.; Watanabe, N.; Hashimoto, S. J. Am. Chem. Soc. 1999, 121, 1417.
7. (c) Padwa, A.; Precedo, L.; Semones, M. A. J. Org. Chem. 1999, 64, 4079.
8. (d) Hamaguchi, M.; Matsubara, H.; Nagai, T. J. Org. Chem. 2001, 66, 5395.
9. (e) Muthusamy, M.; Gunanthan, C.; Suresh, E. Tetrahedron 2004, 60, 7885.
10. (f) Torssell, S.; Somfai, P. Adv. Synth. Catal. 2006, 348, 2421.
11. (g) Galliford, C. V.; Scheidt, K. A. J. Org. Chem. 2007, 72, 1811.
12. (h) Shi, J.; Zhao, M.; Lei, M.; Shi, M. J. Org. Chem. 2008, 73, 305.
13. (i) England, D. B.; Eagan, J. M.; Merey, G.; Anac, O.; Padwa, A. Tetrahedron 2008, 64, 988.
14. (j) England, D. B.; Padwa, A. J. Org. Chem. 2008, 73, 2792.
15. (3)(a) de March, P.; Huisgen, R. J. Am. Chem. Soc. 1982, 104, 4952.
16. (b) de March, P.; Huisgen, R. J. Am. Chem. Soc. 1982, 104, 4953.
17. (c) Alt, M.; Mass, G. Tetrahedron 1994, 50, 7435.
18. (d) Lu, C.-D.; Chen, Z.-Y.; Liu, H.; Hu, W.-H.; Mi, A.-Q.; Doyle, M. P. J. Org. Chem. 2004, 69, 4856.
19. (e) Skaggs, A. J.; Lin, E. Y.; Jamison, T. F. Org. Lett. 2002, 4, 2277.
20. (f) Muthusamy, S.; Gunanathan, C.; Nethaji, M. J. Org. Chem. 2004, 69, 5631.
21. (g) Nair, V.; Mathai, S.; Varma, R. L. J. Org. Chem. 2004, 69, 1413.
22. For the stereospecific synthesis of tetrahydrofuran derivatives by the Lewis acid catalyzed cycloadditions of aldehydes and donor-acceptor cyclopropanes, see: (h) Pohlhaus, P. D.; Sanders, S. D.; Parsons, A. T.; Li, W.; Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 8642.
23. a) Doyle, M. P.; Forbes, D. C.; Protopopova, M. N.; Stanley, S. A.; Vasbinder, M. M.; Xavier, K. R. J. Org. Chem. 1997, 62, 7210.
24. (b) Russell, A. E.; Brekan, J.; Gronenberg, L.; Doyle, M. P. J. Org. Chem. 2004, 69, 5269.
25. (c) Jiang, B.; Zhang, X.; Luo, Z. Org. Lett. 2002, 4, 2453.
26. (d) Alt, M.; Mass, G. Tetrahedron 1994, 50, 7435.
27. (e) Wenkert, E.; Khatuya, H. Tetrahedron Lett. 1999, 40, 5439.
28. (f) DeAngelis, A.; Panne, P.; Yap, G. P. A.; Fox, J. M. J. Org. Chem. 2008, 73, 1435.
29. For three-component dioxolane formation, see: (a) Nair, V.; Mathai, S.; Nair, S. M.; Rath, N. P. Tetrahedron Lett. 2003, 44, 8407.
30. (b) Nair, V.; Mathai, S.; Mathew, S. C.; Rath, N. P. Tetrahedron 2005, 61, 2849.
31. (c) Lu, C.-D.; Chen, Z.-Y.; Liu, H.; Hu, W.-H.; Mi, A.-Q. Org. Lett. 2004, 6, 3071.
32. For the Rh-catalyzed preparation of (Z)-alkenes via β-hydride elimination, see: (a) Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908, and references therein. For recent studies on suppressing β-hydride elimination through ligand selection, see ref 4f and:
33. (b) Panne, P.; DeAngelis, A.; Fox, J. M. Org. Lett. 2008, 10. 2987.
34. (c) Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22.
35. (7)(a) Minami, K.; Saito, H.; Tsutsui, H.; Nambu, H.; Anada, M.; Hashimoto, S. Adv. Synth. Catal. 2005, 347, 1483.
36. (b) Tsutsui, H.; Abe, T.; Nakamura, S.; Anada, M.; Hashimoto, S. Chem. Pharm. Bull. 2005, 10, 1366.
37. For reactions of carbonyl ylides with cyclopropenes, see: Diev, V. V.; Kostikov, R. R.; Gleiter, R.; Molchanov, A. P. J. Org. Chem. 2006, 71, 4066.
38. We note that functional group tolerance was initially guided by an inhibition study in which various functionalized molecules were added in superstoichiometric amounts to the reaction between tert-butyl 2-diazohydrocinnamate, benzaldehyde, and methyl vinyl ketone (see the Supporting Information).
39. Doyle, M. P.; Hu, W.; Timmons, D. J. Org. Lett. 2001, 3, 933.
40. (b) Davies, H. M. L.; DeMesse, J.Tetrahedron Lett. 2001, 42, 6803.