Cationic rhodium(I) complex-catalyzed [3 + 2] and [2 + 1] cycloadditions of propargyl esters with electron-deficient alkynes and alkenes

Journal of the American Chemical Society

Volumn 132, Issue 23, 2010, Pages 7896-7898

  Shibata, Yu ^a   Noguchi, Keiichi ^a   Tanaka, Ken ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ACRYLAMIDES; CYCLOADDITIONS; CYCLOPROPANATION; DIALKYL ACETYLENEDICARBOXYLATES; DIASTEREO-SELECTIVITY; ELECTRON-DEFICIENT; GOOD YIELD; PROPARGYL; RHODIUM COMPLEXES;

ACETYLENE; CYCLOADDITION; ESTERIFICATION; ESTERS; OLEFINS; RHODIUM;

RHODIUM COMPOUNDS;

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ESTER; PROPARGYL ESTER; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; ELECTRON;

EID: 77953310621     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja102418h     Document Type: Article

References (42)

1. For selected recent reviews, see: Pellissier, H. Tetrahedron 2008, 64, 7041
2. Davies, H. M. L. and Walji, A. M. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A. and Tsuji, J., Eds.; Wiley-VCH: Weinheim, Germany, 2005; p 301.
3. Doyle, M. P. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A. and Tsuji, J., Eds.; Wiley-VCH: Weinheim, Germany, 2005; p 341.
4. Wu, Y.-T., Kurahashi, T., and de Meijere, A. J. Organomet. Chem. 2005, 690, 5900
5. Miller, J. A., Jin, W., and Nguyen, S. T. Angew. Chem., Int. Ed. 2002, 41, 2953
6. Miller, J. A., Gross, B. A., Zhuravel, M. A., Jin, W., and Nguyen, S. T. Angew. Chem., Int. Ed. 2005, 44, 3885
7. Chen, Y., Ruppel, J. V., and Zhang, X. P. J. Am. Chem. Soc. 2007, 129, 12074
8. Zhu, S., Perman, J. A., and Zhang, X. P. Angew. Chem., Int. Ed. 2008, 47, 8460
9. Zhu, S., Ruppel, J. V., Lu, H., Wojtas, L., and Zhang, X. P. J. Am. Chem. Soc. 2008, 130, 5042
10. del Amo, J. C., Mancheno, M. J., Gomez-Gallego, M., and Sierra, M. A. Organometallics 2004, 23, 5021
11. Barluenga, J., Vicente, R., Lopez, L. A., Rubio, E., Tomas, M., and Alvarez-Rua, C. J. Am. Chem. Soc. 2004, 126, 470
12. Barluenga, J., Vicente, R., Lopez, L. A., and Tomas, M. J. Organomet. Chem. 2006, 691, 5642
13. Barluenga, J., Vicente, R., Lopez, L. A., and Tomas, M. J. Am. Chem. Soc. 2006, 128, 7050
14. Rautenstrauch, V. J. Org. Chem. 1984, 49, 950
15. Rautenstrauch, V. Tetrahedron Lett. 1984, 25, 3845
16. Miki, K., Ohe, K., and Uemura, S. Tetrahedron Lett. 2003, 44, 2019
17. Miki, K., Ohe, K., and Uemura, S. J. Org. Chem. 2003, 68, 8505
18. Tenaglia, A. and Marc, S. J. Org. Chem. 2006, 71, 3569
19. Johansson, M. J., Gorin, D. J., Staben, S. T., and Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002
20. Gorin, D. J., Dube, P., and Toste, F. D. J. Am. Chem. Soc. 2006, 128, 14480
21. Gorin, D. J., Watson, I. D. G., and Toste, F. D. J. Am. Chem. Soc. 2008, 130, 3736 For other related cycloadditions, see: Shapiro, N. D. and Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244
22. Shapiro, N. D., Shi, Y., and Toste, F. D. J. Am. Chem. Soc. 2009, 131, 11654
23. For selected recent reviews, see: Gorin, D. J. and Toste, F. D. Nature 2007, 446, 395
24. Kusama, H. and Iwasawa, N. Chem. Lett. 2006, 35, 1082
25. Miki, K., Uemura, S., and Ohe, K. Chem. Lett. 2005, 34, 1068
26. For selected recent examples, see: Lian, Y. and Davies, H. M. L. J. Am. Chem. Soc. 2010, 132, 440
27. Davies, H. M. L., Xiang, B., Kong, N., and Stafford, D. G. J. Am. Chem. Soc. 2001, 123, 7461
28. Shibata, Y., Noguchi, K., Hirano, M., and Tanaka, K. Org. Lett. 2008, 10, 2825
29. Tanaka, K., Okazaki, E., and Shibata, Y. J. Am. Chem. Soc. 2009, 131, 10822
30. Prasad, B. A. B., Yoshimoto, F. K., and Sarpong, R. J. Am. Chem. Soc. 2005, 127, 12468
31. Pujanauski, B. G., Prasad, B. A. B., and Sarpong, R. J. Am. Chem. Soc. 2006, 128, 6786
32. Zhang, G. and Zhang, L. J. Am. Chem. Soc. 2008, 130, 12598
33. Ru(II), Pd(II), Pt(II), and Au(I) complexes failed to catalyze the reaction.
34. When phenyl-substituted propargyl ester 1i was employed, the corresponding cycloaddition products were not obtained at all. The corresponding allene, generated through the 1,3-acyloxy rearrangement, and its hydrolyzed ketone were obtained as major products. The reactions of terminal propargyl ester 1j led to a complex mixture of products
35. We have previously found that acrylamides are suitable coupling partners for the cationic rhodium(I)-catalyzed hydroacylation and cycloaddition. See: Shibata, Y. and Tanaka, K. J. Am. Chem. Soc. 2009, 131, 12552
36. Tanaka, K., Hagiwara, Y., and Noguchi, K. Angew. Chem., Int. Ed. 2005, 44, 7260
37. Trost, B. M. and Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183
38. Tollari, S., Palmisano, G., Cenini, S., Cravotto, G., Giovenzana, G. B., and Penoni, A. Synthesis 2001, 735
39. Hoye, T. R., Dinsmore, C. J., Johnson, D. S., and Korkowski, P. F. J. Org. Chem. 1990, 55, 4518
40. Davies, H. M. L. and Romines, K. R. Tetrahedron 1988, 44, 3343
41. Indeed, the reaction of 1a with methyl acrylate (5d) furnished cyclopropane 6ad as a single diastereomer, but that with styrene (5e) bearing no carbonyl group furnished cyclopropane 6ae as a mixture of diastereomers, although these products could not be isolated in a pure form
42. The same diastereoselectivity was observed in the Ru(II)- (ref 2) and Co(II)-catalyzed (ref 3a) cyclopropanations of acrylates with 9.