Rhodium-catalyzed conjugate addition of arylindium reagents to α,β-unsaturated carbonyl compounds

Tetrahedron

Volumn 68, Issue 5, 2012, Pages 1606-1611

  Tato, Rubén ^a   Riveiros, Ricardo ^a   Pérez Sestelo, José ^a   Sarandeses, Luis A ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

Conjugate addition; Organoindium compounds; Rhodium

Indexed keywords

ALKENE DERIVATIVE; CARBONYL DERIVATIVE; INDIUM; KETONE DERIVATIVE; LACTONE DERIVATIVE; LIGAND; METHANOL; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; RHODIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

EID: 84855607081     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.11.075     Document Type: Article

References (68)

1. For reviews on synthetic applications of indium, see: P. Cintas Synlett 1995 1087 1096
2. C.-J. Li, and T.-H. Chan Tetrahedron 55 1999 11149 11176
3. B.C. Ranu Eur. J. Org. Chem. 2000 2347 2356
4. J. Podlech, and T.C. Maier Synthesis 2003 633 655
5. V. Nair, S. Ros, C.N. Jayan, and B.S. Pillai Tetrahedron 60 2004 1959 1982
6. J. Augé, N. Lubin-Germain, and J. Uziel Synthesis 2007 1739 1764
7. J.S. Yadav, A. Antony, J. George, and B.V.S. Reddy Eur. J. Org. Chem. 2010 591 605
8. I. Pérez, J. Pérez Sestelo, M.A. Maestro, A. Mouriño, and L.A. Sarandeses J. Org. Chem. 63 1998 10074 10076
9. I. Pérez, J. Pérez Sestelo, and L.A. Sarandeses Org. Lett. 1 1999 1267 1269
10. I. Pérez, J. Pérez Sestelo, and L.A. Sarandeses J. Am. Chem. Soc. 123 2001 4155 4160
11. M.A. Pena, I. Pérez, J. Pérez Sestelo, and L.A. Sarandeses Chem. Commun. 2002 2246 2247
12. M.A. Pena, J. Pérez Sestelo, and L.A. Sarandeses Synthesis 2003 780 784
13. M.A. Pena, J. Pérez Sestelo, and L.A. Sarandeses Synthesis 2005 485 492
14. M.A. Pena, J. Pérez Sestelo, and L.A. Sarandeses J. Org. Chem. 72 2007 1271 1275
15. J. Caeiro, J. Pérez Sestelo, and L.A. Sarandeses Chem. - Eur. J. 14 2008 741 746
16. R. Riveiros, L. Saya, J. Pérez Sestelo, and L.A. Sarandeses Eur. J. Org. Chem. 2008 1959 1966
17. A. Mosquera, R. Riveiros, J. Pérez Sestelo, and L.A. Sarandeses Org. Lett. 10 2008 3745 3748
18. L. Bouissane, J. Pérez Sestelo, and L.A. Sarandeses Org. Lett. 11 2009 1285 1288
19. D. Rodríguez, J. Pérez Sestelo, and L.A. Sarandeses J. Org. Chem. 68 2003 2518 2520
20. D. Rodríguez, J. Pérez Sestelo, and L.A. Sarandeses J. Org. Chem. 69 2004 8136 8139
21. R. Riveiros, D. Rodríguez, J. Pérez Sestelo, and L.A. Sarandeses Org. Lett. 8 2006 1403 1406
22. R. Riveiros, J. Pérez Sestelo, and L.A. Sarandeses Synthesis 2007 3595 3598
23. K. Takami, H. Yorimitsu, H. Shinokubo, S. Matsubara, and K. Oshima Org. Lett. 3 2001 1997 1999
24. P.H. Lee, S.W. Lee, and K. Lee Org. Lett. 5 2003 1103 1106
25. U. Lehmann, S. Awasthi, and T. Minehan Org. Lett. 5 2003 2405 2408
26. M. Barbero, S. Cadamuro, S. Dughera, and C. Giaveno Eur. J. Org. Chem. 2006 4884 4890
27. E. Font-Sanchis, F.J. Céspedes-Guirao, A. Sastre-Santos, and F. Fernández-Lázaro J. Org. Chem. 72 2007 3589 3591
28. W. Lee, Y. Kang, and P.H. Lee J. Org. Chem. 73 2008 4326 4329
29. L. Zhang, Y. Luo, and J. Wu Synlett 2010 1845 1848
30. P. Perlmutter Conjugate Addition Reactions in Organic Synthesis 1992 Pergamon Oxford, UK
31. J.A. Kozlowski B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 4 1991 Pergamon Oxford, UK Chapter 1.4, pp 169-198
32. A. Alexakis M. Beller, C. Bolm, Transition Metals for Organic Synthesis Vol. 1 1998 Wiley-VCH Weinheim Chapter 3.10, pp 504-513
33. T. Hayashi, and K. Yamasaki Chem. Rev. 103 2003 2829 2844
34. K. Fagnou, and M. Lautens Chem. Rev. 103 2003 169 196
35. A.S.C. Chan, F.Y. Kwong, and G. Lu D.M.P. Mingos, R.H. Crabtree, Comprehensive Organometallic Chemistry III Vol. 10 2007 Elsevier Oxford, UK Chapter 10.08, pp 369-401
36. M. Pucheault, S. Darses, and J.-P. Genêt Eur. J. Org. Chem. 2002 3552 3557
37. H.J. Edwards, J.D. Hargrave, S.D. Penrose, and C.G. Frost Chem. Soc. Rev. 39 2010 2093 2105
38. For a review, see: J.D. Hargrave, J.C. Allen, and C.G. Frost Chem. - Asian J. 5 2010 386 396
39. T. Miura, and M. Murakami Chem. Commun. 2005 5676 5677
40. H.C. Clark, and A.L. Pickard J. Organomet. Chem. 8 1967 427 434
41. O.T. Beachley Jr., and R.N. Rusinko Inorg. Chem. 18 1979 1966 1968
42. H. Schumann, U. Hartmann, and W. Wassermann Polyhedron 9 1990 353 360
43. R.C. Crittendon, B.C. Beck, J. Su, X.-W. Li, and G.H. Robinson Organometallics 18 1999 156 160
44. Y.-H. Chen, and P. Knochel Angew. Chem., Int. Ed. 47 2008 7648 7651
45. V. Papoian, and T. Minehan J. Org. Chem. 73 2008 7376 7379
46. The indium present in the reaction media could be recovered by electrochemical deposition, see: R.H. Prenner, W.H. Binder, and W. Schmid Liebigs Ann. Chem. 1994 73 78
47. T. Hayashi, M. Takahashi, Y. Takaya, and M. Ogasawara J. Am. Chem. Soc. 124 2002 5052 5058
48. Y.-H. Chen, M. Sun, and P. Knochel Angew. Chem., Int. Ed. 48 2009 2236 2239
49. For the use of MeOH in conjugate addition reactions of boron reagents to α,β-unsaturated compounds, see: K. Hirano, H. Yorimitsu, and K. Oshima Org. Lett. 9 2007 1541 1544
50. R. Shintani, Y. Tsutsumi, M. Nagaosa, T. Nishimura, and T. Hayashi J. Am. Chem. Soc. 131 2009 13588 13589
51. 13C NMR accordingly to the literature, see Ref. 6a and: L. Adak, and N. Yoshikai J. Org. Chem. 76 2011 7563 7568 For further experimental details see Supplementary data
52. For further details, see the Supplementary data.: M. Yasuda, M. Haga, and A. Baba Organometallics 28 2009 1998 2000
53. M. Yasuda, M. Haga, and A. Baba Eur. J. Org. Chem. 2009 5513 5517
54. M. Yasuda, M. Haga, Y. Nagaoka, and A. Baba Eur. J. Org. Chem. 2010 5359 5363
55. M. Yasuda, K. Kiyokawa, K. Osaki, and A. Baba Organometallics 28 2009 132 139
56. K. Kiyokawa, M. Yasuda, and A. Baba Organometallics 30 2011 2039 2043
57. Y. Nishimoto, R. Moritoh, M. Yasuda, and A. Baba Angew. Chem., Int. Ed. 48 2009 4577 4580
58. Z.-L. Shen, K.K.K. Goh, H.-L. Cheong, C.H.A. Wong, Y.-C. Lai, Y.-S. Yang, and T.-P. Loh J. Am. Chem. Soc. 132 2010 15852 15855
59. S.H. Bertz, and G. Dabbagh Tetrahedron 45 1989 425 434
60. A.S. Cieplak, B.D. Tait, and C.R. Johnson J. Am. Chem. Soc. 111 1989 8447 8462
61. J.-G. Boiteau, R. Imbos, A.J. Minnaard, and B.L. Feringa Org. Lett. 5 2003 681 684
62. Y. Takaya, M. Ogasawara, and T. Hayashi J. Am. Chem. Soc. 120 1998 5579 5580
63. Y. Takaya, M. Ogasawara, and T. Hayashi Tetrahedron Lett. 40 1999 6957 6961
64. C.-G. Feng, Z.-Q. Wang, P. Tian, M.-H. Xu, and G.-Q. Lin Chem. - Asian J. 3 2008 1511 1516
65. Y. Ma, C. Song, C. Ma, Z. Sun, Q. Chai, and M.B. Andrus Angew. Chem., Int. Ed. 42 2003 5871 5874
66. Q. Chen, M. Kuriyama, X. Hao, T. Soeta, Y. Yamamoto, K. Yamada, and K. Tomioka Chem. Pharm. Bull. 57 2009 1024 1027
67. Y. Takaya, T. Senda, H. Kurushima, M. Ogasawara, and T. Hayashi Tetrahedron: Asymmetry 10 1999 4047 4056
68. A. Fryszkowska, M. Komar, D. Koszelewski, and R. Ostaszewski Tetrahedron: Asymmetry 16 2005 2475 2485