Enantioselective synthesis of cyclobutanes via sequential Rh-catalyzed bicyclobutanation/Cu-catalyzed homoconjugate addition

Journal of the American Chemical Society

Volumn 135, Issue 25, 2013, Pages 9283-9286

  Panish, Robert ^a   Chintala, Srinivasa R ^a   Boruta, David T ^a   Fang, Yinzhi ^a   Taylor, Michael T ^a   Fox, Joseph M ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYZED REACTIONS; CYCLIZATION PRODUCTS; CYCLOBUTANES; DIASTEREO-SELECTIVITY; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZED; THREE-COMPONENT;

CATALYSIS; CYCLIZATION; ENANTIOMERS; RHODIUM;

ENANTIOSELECTIVITY;

COPPER; CYCLOBUTANE DERIVATIVE; GRIGNARD REAGENT;

ADDITION REACTION; ARTICLE; CYCLOPROPANATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; EPIMERIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COPPER; CYCLIZATION; CYCLOBUTANES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 84879539043     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja403811t     Document Type: Article

References (56)

1. Dembitsky, V. M. J. Nat. Med. 2008, 62, 1
2. Hansen, T. V.; Stenstrøm, Y. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; Elsevier Science: Oxford, U.K., 2001; Vol. 5.
3. Iriondo-Alberdi, J.; Greaney, M. F. Eur. J. Org. Chem. 2007, 2007, 4801
4. Bach, T.; Hehn, J. P. Angew. Chem., Int. Ed. 2011, 50, 1000
5. Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449
6. De Mayo, P. Acc. Chem. Res. 1971, 4, 41
7. Crimmins, M. T. Chem. Rev. 1988, 88, 1453
8. Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3
9. Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2009, 131, 14604
10. Tyson, E. L.; Farney, E. P.; Yoon, T. P. Org. Lett. 2012, 14, 1110
11. Feltenberger, J. B.; Ko, C.; Deng, J.; Ghosh, S. K.; Hsung, R. P. Heterocycles 2012, 84, 843
12. Gassman, P. G.; Chavan, S. P.; Fertel, L. B. Tetrahedron Lett. 1990, 31, 6489
13. Talavera, G.; Reyes, E.; Vicario, J. L.; Carrillo, L. Angew. Chem., Int. Ed. 2012, 51, 4104
14. Hyatt, J.; Raynolds, P. W. Org. React. 1994, 45, 159
15. Brady, W. T. Tetrahedron 1981, 37, 2949
16. Hussain, M. M.; Li, H.; Hussain, N.; Ureña, M.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2009, 131, 6516
17. Trost, B. M.; Keeley, D. E.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 3068
18. Hiroi, K.; Nakamura, H.; Anzai, T. J. Am. Chem. Soc. 1987, 109, 1249
19. Nemoto, H.; Ishibashi, H.; Mori, M.; Fujita, S.; Fukumoto, K. Heterocycles 1990, 31, 1237
20. Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, 7507
21. Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076
22. Hoz, S. In The Chemistry of the Cyclopropyl Group; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1987; p 1121.
23. Wiberg, K. B. Angew. Chem., Int. Ed. Engl. 1986, 25, 312
24. Walczak, M. A.; Wipf, P. J. Am. Chem. Soc. 2008, 130, 6924
25. Walczak, M. A.; Wipf, P. Angew. Chem., Int. Ed. 2006, 45, 4172
26. Wipf, P.; Stephenson, C. R.; Okumura, K. J. Am. Chem. Soc. 2003, 125, 14694
27. Ueda, M.; Walczak, M. A.; Wipf, P. Tetrahedron Lett. 2008, 49, 5986
28. Walczak, M. A.; Shin, B. K.; Wipf, P.; Saxena, S. Org. Biomol. Chem. 2009, 7, 2363
29. Gaoni, Y. Tetrahedron Lett. 1982, 23, 5215
30. Gaoni, Y. J. Org. Chem. 1985, 50, 2948
31. Gaoni, Y. Tetrahedron 1989, 45, 2819
32. Gaoni, Y.; Tomažič, A.; Potgieter, E. J. Org. Chem. 1985, 50, 2943
33. Wiberg, K. B.; Ciula, R. P. J. Am. Chem. Soc. 1959, 81, 5261
34. Hoz, S.; Azran, C.; Sella, A. J. Am. Chem. Soc. 1996, 118, 5456
35. Razin, V. V.; Vasin, V. A.; Blinkov, I. E. Russ. J. Org. Chem. 1993, 29, 759
36. Wiberg, K. B.; Lampman, G. M.; Ciula, R. P.; Connor, D. S.; Schertler, P.; Lavanish, J. Tetrahedron 1965, 21, 2749
37. Boruta, D. T.; Dmitrenko, O.; Yap, G. P. A.; Fox, J. M. Chem. Sci. 2012, 3, 1589
38. DeAngelis, A.; Panne, P.; Yap, G. P. A.; Fox, J. M. J. Org. Chem. 2008, 73, 1435
39. DeAngelis, A.; Dmitrenko, O.; Yap, G. P. A.; Fox, J. M. J. Am. Chem. Soc. 2009, 131, 7230
40. DeAngelis, A.; Dmitrenko, O.; Fox, J. M. J. Am. Chem. Soc. 2012, 134, 11035
41. DeAngelis, A.; Shurtleff, V. W.; Dmitrenko, O.; Fox, J. M. J. Am. Chem. Soc. 2011, 133, 1650
42. DeAngelis, A.; Taylor, M. T.; Fox, J. M. J. Am. Chem. Soc. 2009, 131, 1101
43. Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22
44. Panne, P.; DeAngelis, A.; Fox, J. M. Org. Lett. 2008, 10, 2987
45. Ikota, N.; Takamura, N.; Young, S. D.; Ganem, B. Tetrahedron Lett. 1981, 42, 4163
46. Goto, T.; Takeda, K.; Shimada, N.; Nambu, H.; Anada, M.; Shiro, M.; Ando, K.; Hashimoto, S. Angew. Chem., Int. Ed. 2011, 50, 6803
47. Goto, T.; Takeda, K.; Anada, M.; Ando, K.; Hashimoto, S. Tetrahedron Lett. 2011, 52, 4200
48. Qin, C.; Davies, H. M. Org. Lett. 2013, 15, 310
49. Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett 1996, 85
50. Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Tuladhar, S. M.; Twohig, M. F. J. Chem. Soc., Perkin Trans. 1 1990, 1047
51. Duddeck, H.; Ferguson, G.; Kaitner, B.; Kennedy, M.; McKervey, M. A.; Maguire, A. R. J. Chem. Soc., Perkin Trans. 1 1990, 1055
52. Maguire, A. R.; Buckley, N. R.; O'Leary, P.; Ferguson, G. J. Chem. Soc., Perkin Trans. 1 1998, 4077
53. McDowell, P. A.; Foley, D. A.; O'Leary, P.; Ford, A.; Maguire, A. R. J. Org. Chem. 2012, 77, 2035
54. O'Keeffe, S.; Harrington, F.; Maguire, A. R. Synlett 2007, 2367
55. O'Neill, S.; O'Keeffe, S.; Harrington, F.; Maguire, A. R. Synlett 2009, 2312
56. Reisman, S. E.; Nani, R. R.; Levin, S. Synlett 2011, 2437