Stereoselective restructuring of 3-arylcyclobutanols into 1-indanols by sequential breaking and formation of carbon-carbon bonds

Chemistry - A European Journal

Volumn 15, Issue 47, 2009, Pages 12929-12931

  Shigeno, Masanori ^a   Yamamoto, Taiga ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

1,2 addition; Asymmetric synthesis; C C activation; Indanols; Rhodium

Indexed keywords

ASYMMETRIC SYNTHESIS; C-C ACTIVATIONS; CARBON-CARBON BOND; CARBON-CARBON BOND CLEAVAGE; CARBON-CARBON BOND FORMATION; ELEMENTARY STEPS; ENANTIOSELECTIVE; QUATERNARY CARBON; RHODIUM-CATALYZED; STEREO-SELECTIVE;

ELECTRON TRANSITIONS; RHODIUM;

SYNTHESIS (CHEMICAL);

EID: 73349132334     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902593     Document Type: Article

References (53)

1. a) M. Murakami, Y. Ito, Top. Organomet. Chem. 1999, 3, 97-129;
2. M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759-1792;
3. C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610-618;
4. T. Kondo, T. Mitsudo, Chem. Lett. 2005, 34, 1462-1467.
5. a) T. Kondo, M. Niimi, M. Nomura, K. Wada, T. Mitsudo, Tetrahedron Lett. 2007, 48, 2837-2839;
6. T. Matsuda, T. Tsuboi, M. Murakami, J. Am. Chem. Soc. 2007, 129, 12596-12597;
7. R. Shintani, K. Takatsu, T. Katoh, T. Nishimura, T. Hayashi, Angew. Chem. 2008, 120, 1469-1471;
8. Angew. Chem. Int. Ed. 2008, 47, 1447-1449;
9. S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2008, 130, 5048-5049;
10. M. P. Watson, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 12594-12595;
11. T. Matsuda, M. Shigeno, M. Murakami, Org. Lett. 2008, 10, 5219-5221;
12. M. Tobisu, Y. Kita, Y. Ano, N. Chatani, J. Am. Chem. Soc. 2008, 130, 15982-15989;
13. C. Najera, J. M. Sansano, Angew. Chem. 2009, 121, 2488-2492;
14. Angew. Chem. Int. Ed. 2009, 48, 2452-2456;
15. Y. Hirata, T. Inui, Y. Nakao, T. Hiyama, J. Am. Chem. Soc. 2009, 131, 6624-6631.
16. a) T. Nishimura, S. Matsumura, Y. Maeda, S. Uemura, J. Am. Chem. Soc. 2003, 125, 8862-8869;
17. T. Matsuda, M. Shigeno, M. Makino, M. Murakami, Org. Lett. 2006, 8, 3379-3381;
18. T. Ohmura, H. Taniguchi, Y. Kondo, M. Suginome, J. Am. Chem. Soc. 2007, 129, 3518-3519;
19. B. M. Trost, J. Xie, J. Am. Chem. Soc. 2008, 130, 6231-6242;
20. T. Seiser, N. Cramer, Angew. Chem. 2008, 120, 9435-9438;
21. Angew. Chem. Int. Ed. 2008, 47, 9294-9297;
22. C. Winter, N. Krause, Angew. Chem. Int. Ed. 2009, 48, 2460-2462.
23. T. Matsuda, M. Shigeno, M. Murakami, J. Am. Chem. Soc. 2007, 129, 12086-12087.
24. a) T. Nishimura, S. Uemura, Synlett., 2004, 201-206;
25. T. Satoh, M. Miura, Top. Organomet. Chem. 2005, 14, 1-20;
26. M. Murakami, M. Makino, S. Ashida, T. Matsuda, Bull. Chem. Soc. Jpn. 2006, 79, 1315-1321.
27. A report on a similar reaction appeared on the Web during the preparation of this manuscript: T. Seiser, O. A. Roth, N. Cramer, Angew. Chem. 2009, 121, 6438-6441;
28. Angew. Chem. Int. Ed. 2009, 48, 6320-6323.
29. a) K. Fuji, Chem. Rev. 1993, 93, 2037-2066;
30. E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 2092-2118;
31. Angew. Chem. Int. Ed. 1998, 37, 388-401;
32. J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732;
33. Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
34. I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105-10146;
35. J. D. Christopher, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363-5367;
36. Quaternary Stereocenters (Eds.: J. Christoffers; A. Baro), Wiley-VCH, Weinheim, 2005;
37. T. Rovis in New Frontiers in Asymmetric Catalysis (Eds.: K. Mikami, M. Lautens), Wiley, New York, 2007, pp. 275-311;
38. M. Hatano, K. Ishihara, Synthesis 2008, 1647-1675;
39. M. Shibasaki, M. Kanai, Chem. Rev. 2008, 108, 2853-2873.
40. It was hardly possible to separate the diastereomers by preparative chromatography. The ratio was determined by HPLC analysis.
41. S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, P. Dellis, Angew. Chem. 2004, 116, 324-329;
42. Angew. Chem. Int. Ed. 2004, 43, 320-325.
43. The configuration was (1S, 3R). The enantiopurity of the minor diastereomer was 32% ee with dominance of (1R, 3R) configuration.
44. a) S. Ma, Z. Gu, Angew. Chem. 2005, 117, 7680-7685;
45. Angew. Chem. Int. Ed. 2005, 44, 7512-7517;
46. Q. Huang, A. Fazio, G. Dai, M. A. Campo, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 7460-7461.
47. a) M. Sakai, M. Ueda, N. Miyaura, Angew. Chem. 1998, 110, 3475-3477;
48. Angew. Chem. Int. Ed. 1998, 37, 3279-3281;
49. H.-F. Duan, J.-H. Xie, W.-J. Shi, Q. Zhang, Q.-L. Zhou, Org. Lett. 2006, 8, 1479-1481;
50. K. Suzuki, S. Ishii, K. Kondo, T. Aoyama, Synlett 2006, 648-650;
51. G. Liu, X. Lu, J. Am. Chem. Soc. 2004, 126, 7460-7461.
52. The reaction of cis-1h required higher temperature than trans-1h.
53. See the Supporting Information for details.