Rh-catalyzed π-facial selective intermolecular hydroacylation of norbornenes

Tetrahedron Letters

Volumn 46, Issue 36, 2005, Pages 6053-6056

  Tanaka, Keitaro ^a   Tanaka, Masakazu ^a   Suemune, Hiroshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Facial selection; C C forming reaction; C H activation; Hydroacylation; Norbornene; Rh complex

Indexed keywords

7 TERT BUTOXYNORBORNADIENE; DEUTERIUM; FUNCTIONAL GROUP; NORBORNADIENE DERIVATIVE; NORBORNENE DERIVATIVE; RHODIUM; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CHELATION; CHEMICAL LABELING; HYDROGENATION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 23244446232     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.004     Document Type: Article

References (43)

1. B.M. Trost Science 254 1991 1471 1477
2. B. Breit, and W. Seiche Synthesis 2001 1 36
3. V. Ritleng, C. Sirlin, and M. Pfeffer Chem. Rev. 102 2002 1731 1769
4. M. Beller, C. Breindl, M. Eichberger, C.G. Hartung, J. Seayad, O.R. Thiel, A. Tillack, and H. Trauthein Synlett 2002 1579 1594
5. Y. Nishihara, Y. Inoue, M. Itazaki, and K. Takagi Org. Lett. 7 2005 2639 2641
6. R.W. Jordan, P.R. Khoury, J.D. Goddard, and W. Tam J. Org. Chem. 69 2004 8467 8474
7. K. Fugami, Y. Hirunuma, T. Nishikata, D. Koyama, M. Kameyama, and M. Kosugi J. Organomet. Chem. 687 2003 567 569
8. R. Kumareswaran, M. Nandi, and T.V. RajanBabu Org. Lett. 5 2003 4345 4348
9. R. Rios, M.A. Pericas, A. Moyano, M.A. Maestro, and J. Mahia Org. Lett. 4 2002 1205 1208
10. P. Mayo, and W. Tam Tetrahedron 58 2002 9527 9540
11. S. Ko, Y. Na, and S. Chang J. Am. Chem. Soc. 124 2002 750 751
12. K. Oguma, M. Miura, T. Satoh, and M. Nomura J. Am. Chem. Soc. 122 2000 10464 10465
13. J.J. Brunet, G. Commenges, D. Neibecker, and K. Philippot J. Organomet. Chem. 469 1994 221 228
14. S. Torii, H. Okumoto, H. Ozaki, S. Nakayasu, and T. Kotani Tetrahedron Lett. 31 1990 5319 5322
15. See Rh-catalyzed intramolecular hydroacylations: K. Sakai, J. Ide, O. Oda, and N. Nakamura Tetrahedron Lett. 1972 1287 1290
16. Y. Taura, M. Tanaka, W.-M. Wu, K. Funakoshi, and K. Sakai Tetrahedron 47 1991 4879 4888
17. M. Tanaka, M. Imai, M. Fujio, E. Sakamoto, M. Takahashi, Y. Eto-Kato, W.-M. Wu, K. Funakoshi, K. Sakai, and H. Suemune J. Org. Chem. 65 2000 5806 5816
18. A.D. Aloise, M.E. Layton, and M.D. Shair J. Am. Chem. Soc. 122 2000 12610 12611
19. Y. Sato, Y. Oonishi, and M. Mori Angew. Chem., Int. Ed. 41 2002 1218 1221
20. K. Tanaka, and G.C. Fu J. Am. Chem. Soc. 125 2003 8078 8079
21. M. Tanaka, K. Sakai, and H. Suemune Curr. Org. Chem. 7 2003 353 367
22. K. Tanaka J. Synth. Org. Chem. Jpn. 63 2005 351 358 and references cited therein
23. C.-H. Jun, C.W. Moon, and D.-Y. Lee Chem. Eur. J. 8 2002 2422 2428
24. C.-H. Jun, C.W. Moon, H. Lee, and D.-Y. Lee J. Mol. Catal. A: Chem. 189 2002 145 156
25. C.-H. Jun, J.-B. Hong, and D.-Y. Lee Synlett 1999 1 12
26. M.C. Willis, S.J. McNally, and P.J. Beswick Angew. Chem., Int. Ed. 43 2004 340 343
27. M.C. Willis, H.E. Randell-Sly, R.L. Woodward, and G.S. Currie Org. Lett. 7 2005 2249 2251
28. M. Tanaka, M. Imai, Y. Yamamoto, K. Tanaka, M. Shimowatari, S. Nagumo, N. Kawahara, and H. Suemune Org. Lett. 5 2003 1365 1367
29. M. Imai, M. Tanaka, K. Tanaka, Y. Yamamoto, N. Imai-Ogata, M. Shimowatari, S. Nagumo, N. Kawahara, and H. Suemune J. Org. Chem. 69 2004 1144 1150
30. K. Kokubo, K. Matsumasa, Y. Nishinaka, M. Miura, and M. Nomura Bull. Chem. Soc. Jpn. 72 1999 303 311
31. C.K. Brown, and G. Wilkinson Tetrahedron Lett. 1969 1725 1726
32. C.K. Brown, and G. Wilkinson J. Chem. Soc., A 1970 2753 2764
33. CCDC-260662, 260663, and 260664 contain the supplementary crystallographic data for this letter. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk ).
34. 2Cl was heated at 80°C, endo-7 was partly converted into exo-7.
35. 3; flow rate, 3.8 mL/min).
36. P.R. Story J. Org. Chem. 26 1961 287 290
37. P.R. Story, and S.R. Fahrenholtz J. Org. Chem. 28 1963 1716 1717
38. The syn/anti nomenclature is based on the reacted olefin of 7-substituted NBDs.
39. K.N. Houk, P.H. Mueller, Y.-D. Wu, P.H. Mazzocchi, D. Shook, and F. Khachik Tetrahedron Lett. 31 1990 7285 7288
40. M. Lautens, W. Tam, and L. Edwards J. Chem. Soc., Perkin Trans. 1 1994 2143 2147
41. A.S. Cieplak Chem. Rev. 99 1999 1265 1336
42. T. Ohwada Chem. Rev. 99 1999 1337 1375
43. The stability and reactivity of Rh-substrate intermediates would affect the d-content % of products.