Functionalization of acetalic C(sp3)-H bonds by scandium(III) triflate-catalyzed intramolecular redox reactions: Tandem 1,4-hydride transfer/1,5-cyclization processes leading to protected 1-indanones

Advanced Synthesis and Catalysis

Volumn 353, Issue 4, 2011, Pages 557-562

  Alajarin, Mateo ^a   Marin Luna, Marta ^a   Vidala, Angel ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

1,4 H shift; Acetals; Cyclization; Intramolecular hydride transfer; Scandium triflate

Indexed keywords

EID: 79952553884     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000812     Document Type: Article

References (46)

1. For a recent collection of reviews see the monographic issue number 2 of Chem. Rev. 2010 on the topic "Selective Functionalization of C-H Bonds".
2. For a review, see: K. Godula, D. Sames, Science 2006, 312, 67.
3. For some recent reviews, see: M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704;
4. M. Albrecht, Chem. Rev. 2010, 110, 576;
5. M. M. Diaz-Requejo, P. J. Perez, Chem. Rev. 2008, 108, 3379;
6. H. M. L. Davies, J. R. Manning, Nature 2008, 451, 417;
7. K. R. Campos, Chem. Soc. Rev. 2007, 36, 1069;
8. H. M. L. Davies, M. S. Long, Angew. Chem. 2005, 117, 3584;
9. Angew. Chem. Int. Ed. 2005, 44, 3518.
10. For a pertinent highlight of this methodology see: M. Tobisu, N. Chatani, Angew. Chem. 2006, 118, 1713;
11. Angew. Chem. Int. Ed. 2006, 45, 1683.
12. For some recent examples see: G. Zhou, J. Zhang, Chem. Commun. 2010, 6593;
13. Y. K. Kang, S. M. Kim, D. Y. Kim, J. Am. Chem. Soc. 2010, 132, 11847;
14. S. Murarka, I. Deb, C. Zhang, D. Seidel, J. Am. Chem. Soc. 2009, 131, 13226;
15. S. Murarka, C. Zhang, M. D. Konieczynska, D. Seidel, Org. Lett. 2009, 11, 129;
16. J. C. Ruble, A. R. Hurd, T. A. Johnson, D. A. Sherry, M. R. Baebachyn, P. L. Toogood, G. L. Bundy, D. R. Graber, G. M. Kamilar, J. Am. Chem. Soc. 2009, 131, 3991;
17. J. Barluenga, M. Fañanas-Mastral, F. Aznar, C. Valdes, Angew. Chem. 2008, 120, 6696;
18. Angew. Chem. Int. Ed. 2008, 47, 6594.
19. K. Mori, T. Kawasaki, S. Sueoka, T. Akiyama, Org. Lett. 2010, 12, 1732;
20. I. D. Jurberg, Y. Odabachian, F. Gagosz, J. Am. Chem. Soc. 2010, 132, 3543;
21. D. Shikanai, H. Murase, T. Hata, H. Urabe, J. Am. Chem. Soc. 2009, 131, 3166;
22. P. A. Vadola, D. Sames, J. Am. Chem. Soc. 2009, 131, 16525;
23. K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2009, 131, 402;
24. K. M. McQuaid, J. Z. Long, D. Sames, Org. Lett. 2009, 11, 2972;
25. S. J. Pastine, D. Sames, Org. Lett. 2005, 7, 5429;
26. S. J. Pastine, K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2005, 127, 12180.
27. S. Yang, Z. Li, X. Lian, C. He, Angew. Chem. 2009, 121, 4059;
28. Angew. Chem. Int. Ed. 2009, 48, 3999;
29. S. J. Mahoney, D. T. Moon, J. Hollinger, E. Fillion, Tetrahedron Lett. 2009, 50, 4706;
30. M. Tobisu, H. Nakai, N. Chatani, J. Org. Chem. 2009, 74, 5471.
31. M. Alajarin, B. Bonillo, M.-M. Ortin, P. Sanchez-Andrada, A. Vidal, Org. Lett. 2006, 8, 5645;
32. M. Alajarin, B. Bonillo, P. Sanchez-Andrada, A. Vidal, D. Bautista, Org. Lett. 2009, 11, 1365;
33. M. Alajarin, B. Bonillo, P. Sanchez-Andrada, A. Vidal, J. Org. Chem. 2010, 75, 3737;
34. M. Alajarin, B. Bonillo, M.-M. Ortin, P. Sanchez-Andrada, A. Vidal, R.-A. Orenes, Org. Biomol. Chem. 2010, 8, 4690.
35. G. D. Hartman, B. T. Phillips, W. Halcenko, J. Org. Chem. 1985, 50, 2423.
36. For a recent review on alkene hydroacylations, see: M. C. Willis, Chem. Rev. 2010, 110, 725.
37. Although the intramolecular hydroacylation of olefins has been actively studied during the last two decades, the use of this method for introducing quaternary carbons has been rarely reported, see: B. M. Trost, C. Jiang, Synthesis 2006, 369;
38. M. Tanaka, M. Imai, M. Fujio, E. Sakamoto, M. Takahashi, Y. Eto-Kato, X. M. Wu, K. Funakoshi, K. Sakai, H. Suemune, J. Org. Chem. 2000, 65, 5806;
39. M. Tanaka, M. Takahashi, E. Sakamoto, M. Imai, A. Matsui, M. Fujio, K. Funakoshi, K. Sakai, H. Suemune, Tetrahedron 2001, 57, 1197.
40. K. Kundu, J. V. McCullagh, A. T. Morehead Jr, J. Am. Chem. Soc. 2005, 127, 16042.
41. K. Benda, W. Regenhardt, E. Schaumann, G. Adiwidjaja, Eur. J. Org. Chem. 2009, 1016.
42. A. T. Khan, E. Mondal, S. Ghosh, S. Islam, Eur. J. Org. Chem. 2004, 2002.
43. A high electronegativity at the migrating center is in accord with the classical ideas of an anionotropic migration, see, for instance: H. Meier, K.-P. Zeller, Angew. Chem. 1975, 87, 52;
44. Angew. Chem. Int. Ed. Engl. 1975, 14, 32.
45. 13C NMR spectra of a similar case (cis- and trans-1,1-dicarbomethoxy-3,4-dimethylcyclopentane), see: D. P. Curran, W. Shen, J. Am. Chem. Soc. 1993, 115, 6051;
46. N. S. Perch, P. Kisanga, R. A. Widenhoefer, Organometallics 2000, 19, 2541.