Exploitation of Rh(i)-Rh(iii) cycles in enantioselective C-C bond cleavages: Access to β-tetralones and benzobicyclo[2.2.2]octanones

Chemical Science

Volumn 5, Issue 2, 2014, Pages 837-840

  Souillart, Laetitia ^a   Cramer, Nicolai ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; C-C BOND CLEAVAGES; CARBON ELIMINATIONS; CYCLOADDITIONS; CYCLOPENTENES; ENANTIOSELECTIVE; OXIDATIVE ADDITIONS; STEREOGENIC CENTERS;

ENANTIOSELECTIVITY;

RHODIUM;

EID: 84891423897     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc52753k     Document Type: Article

References (58)

1. For recent reviews on C-C bond activation, see: (a) B. Rybtchinski and D. Milstein, Angew. Chem., Int. Ed., 1999, 38, 870-883;
2. (b) M. Murakami and Y. Ito, in Activation of Unreactive Bonds and Organic Synthesis, Vol. 3, Top. Organomet. Chem., Springer, 1999, vol. 3, pp. 97-129;
3. (c) M. E. van der Boom and D. Milstein, Chem. Rev., 2003, 103, 1759-1792;
4. (d) C.-H. Jun, Chem. Soc. Rev., 2004, 33, 610-618;
5. (e) T. Satoh and M. Miura, in Palladium in Organic Synthesis, Vol. 14, Top. Organomet. Chem., Springer, 2005, vol. 14, p. 1;
6. (f) T. Kondo and T. Mitsudo, Chem. Lett., 2005, 1462-1467;
7. (g) D. Necas and M. Kotora, Curr. Org. Chem., 2007, 11, 1566-1591;
8. (h) M. Murakami and T. Matsuda, Chem. Commun., 2011, 47, 1100-1105;
9. (i) C. Aissa, Synthesis, 2011, 3389-3407;
10. (j) A. Korotvicka, D. Necas and M. Kotora, Curr. Org. Chem., 2012, 16, 1170-1214.
11. For overviews, see: (a) T. Seiser, T. Saget, D. N. Tran and N. Cramer, Angew. Chem., Int. Ed., 2011, 50, 7740-7752;
12. (b) N. Cramer and T. Seiser, Synlett, 2011, 449-460;
13. (c) T. Seiser and N. Cramer, Org. Biomol. Chem., 2009, 7, 2835-2840;
14. (d) M. Murakami, M. Makino, S. Ashida and T. Matsuda, Bull. Chem. Soc. Jpn., 2006, 79, 1315-1321;
15. (e) P. Zhao, C. D. Incarvito and J. F. Hartwig, J. Am. Chem. Soc., 2006, 128, 3124-3125.
16. (a) T. Matsuda, M. Shigeno, M. Makino and M. Murakami, Org. Lett., 2006, 8, 3379-3381;
17. (b) T. Matsuda, M. Shigeno and M. Murakami, J. Am. Chem. Soc., 2007, 129, 12086-12087;
18. (c) T. Seiser and N. Cramer, Angew. Chem., Int. Ed., 2008, 47, 9294-9297;
19. (d) T. Seiser, O. A. Roth and N. Cramer, Angew. Chem., Int. Ed., 2009, 48, 6320-6323;
20. (e) M. Shigeno, T. Yamamoto and M. Murakami, Chem.-Eur. J., 2009, 15, 12929-12931;
21. (f) T. Seiser and N. Cramer, Chem.-Eur. J., 2010, 16, 3383-3391;
22. (g) T. Seiser and N. Cramer, J. Am. Chem. Soc., 2010, 132, 5340-5341;
23. (h) T. Seiser and N. Cramer, Angew. Chem., Int. Ed., 2010, 49, 10163-10167;
24. (i) T. Seiser, G. Cathomen and N. Cramer, Synlett, 2010, 1699-1703;
25. (j) M. Waibel and N. Cramer, Chem. Commun., 2011, 47, 346-348;
26. (k) N. Ishida, S. Sawano and M. Murakami, Chem. Commun., 2012, 48, 1973-1975;
27. (l) T. Xu, H. M. Ko, N. A. Savage and G. Dong, J. Am. Chem. Soc., 2012, 134, 20005-20008.
28. (a) T. Nishimura, S. Matsumura, Y. Maeda and S. Uemura, Chem. Commun., 2002, 50-51;
29. (b) S. Matsumura, Y. Maeda, T. Nishimura and S. Uemura, J. Am. Chem. Soc., 2003, 125, 8862-8869;
30. (c) M. Waibel and N. Cramer, Angew. Chem., Int. Ed., 2010, 49, 4455-4458.
31. L. Liu, N. Ishida and M. Murakami, Angew. Chem., Int. Ed., 2012, 51, 2485-2488.
32. (a) H.Nemoto,M. Yoshida and K. Fukumoto, J. Org. Chem., 1997, 62, 6450-6451;
33. (b) T. Nishimura and S. Uemura, J. Am. Chem. Soc., 1999, 121, 11010-11011;
34. (c) R. C. Larock and C. K. Reddy, J. Org. Chem., 2002, 67, 2027-2033;
35. (d) M. Yoshida, K. Sugimoto and M. Ihara, Org. Lett., 2004, 6, 1979-1982;
36. (e) M. Ethirajan, H.-S. Oh and J. K. Cha, Org. Lett., 2007, 9, 2693-2696;
37. (f) T. Matsuda, M. Shigeno and M. Murakami, Org. Lett., 2008, 10, 5219-5221;
38. (g) A. Chtchemelinine, D. Rosa and A. Orellana, J. Org. Chem., 2011, 76, 9157-9162;
39. (h) A. Ziadi and R. Martin, Org. Lett., 2012, 14, 1266-1269.
40. For examples of Rh(I)-Rh(III) redox processes in crosscoupling reactions, see: (a) R. C. Larock, K. Narayanan and S. S. Hershberger, J. Org. Chem., 1983, 48, 4377-4380;
41. (b) K. Ueura, T. Satoh and M. Miura, Org. Lett., 2005, 7, 2229-2231;
42. (c) M. L. Kantam, S. Roy, M. Roy, B. Sreedhar, B. M. Choudary and R. L. De, J. Mol. Catal. A: Chem., 2007, 273, 26-31;
43. (d) L. Zhang and J. Wu, Adv. Synth. Catal., 2008, 350, 2409-2413;
44. (e) J.-Y. Yu and R. Kuwano, Angew. Chem., Int. Ed., 2009, 48, 7217-7220.
45. (a) D. L. J. Broere and E. Ruijter, Synthesis, 2012, 44, 2639-2672;
46. (b) G. Dominguez and J. Perez-Castells, Chem. Soc. Rev., 2011, 40, 3430-3444;
47. (c) B. Heller and M. Hapke, Chem. Soc. Rev., 2007, 36, 1085-1094;
48. (d) S. Kotha, E. Brahmachary and K. Lahiri, Eur. J. Org. Chem., 2005, 4741-4767;
49. (e) M. Rubin, A. W. Sromek and V. Gevorgyan, Synlett, 2003, 2265-2291;
50. (f) S. Saito and Y. Yamamoto, Chem. Rev., 2000, 100, 2901-2916.
51. For examples of Pd-catalyzed formation of benzocyclobutane derivatives, see: (a) O. Baudoin, A. Herrbach and F. Guéritte, Angew. Chem., Int. Ed., 2003, 42, 5736-5740;
52. (b) M. Chaumontet, R. Piccardi, N. Audic, J. Hitce, J.-L. Peglion, E. Clot and O. Baudoin, J. Am. Chem. Soc., 2008, 130, 15157-15166;
53. (c) P. Álvarez-Bercedo, A. Flores- Gaspar, A. Correa and R. Martin, J. Am. Chem. Soc., 2010, 132, 466-467;
54. (d) A. Flores-Gaspar, A. Gutiérrez-Bonet and R. Martin, Org. Lett., 2012, 14, 5234-5237.
55. For the incorporation of olefins in Rh(III)-intermediates, see: (a) A.M. Dreis and C. J. Douglas, J. Am. Chem. Soc., 2008, 131, 412-413;
56. (b) M. T. Wentzel, V. J. Reddy, T. K. Hyster and C. J. Douglas, Angew. Chem., 2009, 121, 6237-6239.
57. T. Volpe, G. Revial, M. Pfau and J. d'Angelo, Tetrahedron Lett., 1987, 28, 2367-2370.
58. M. Tobisu, J. Hasegawa, Y. Kita, H. Kinuta and N. Chatani, Chem. Commun., 2012, 48, 11437-11439.