A silicon-position dependent 6-endo-trig cyclization during Tsuji-Trost alkylation

Tetrahedron

Volumn 69, Issue 45, 2013, Pages 9398-9405

  Agarwal, Jyoti ^a   Commandeur, Claude ^a   Malacria, Max ^a   Thorimbert, Serge ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Cyclization; Palladium; Regioselectivity; Silicon derivatives; Tsuji Trost alkylation

Indexed keywords

CYCLOHEXENE DERIVATIVE; LIGAND; PALLADIUM COMPLEX; SILICON; SOLVENT;

ALKYLATION; ARTICLE; CATALYSIS; CYCLIZATION; ELIMINATION REACTION; HYDROSILYLATION; PRIORITY JOURNAL; REACTION OPTIMIZATION; SCREENING; SOLVENT EFFECT; TEMPERATURE; TSUJI TROST ALKYLATION;

EID: 84884672911     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.08.080     Document Type: Article

References (75)

1. Books on palladium-catalyzed reactions
2. J. Tsuji Palladium Reagents and Catalysis: Innovations in Organic Synthesis 1995 Wiley Chichester, UK
3. J. Tsuji Perspectives in Organopalladium Chemistry for the 21st Century 1999 Elsevier Amsterdam, The Netherlands
4. J. Tsuji Palladium Reagents and Catalysis, New Perspectives for the 21st Century 2004 Wiley Chichester, UK
5. E. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis 2002 John Wiley & Sons New York, NY
6. J. Tsuji, H. Takahashi, and M. Morikawa Tetrahedron Lett. 1965 4387 4388
7. B.M. Trost, and T.J. Fullerton J. Am. Chem. Soc. 95 1973 292 294
8. B.M. Trost, and T.J. Dietsch J. Am. Chem. Soc. 95 1973 8200 8201
9. B.M. Trost, and M.L. Crawley Chem. Rev. 103 2003 2921 2943
10. J.D. Weaver, A. Recio, A.J. Grenning, and J.A. Tunge Chem. Rev. 111 2011 1846 1913
11. J. Magano, and J.R. Dunetz Chem. Rev. 111 2011 2177 2250
12. B.M. Trost Org. Process Res. Dev. 16 2012 185 194
13. A. Lumbroso, M.L. Cooke, and B. Breit Angew. Chem., Int. Ed. 52 2013 1890 1932
14. M. Bandini, G. Cera, and M. Chiarucci Synthesis 2012 504 512
15. See also: K. Ohmatsu, M. Ito, T. Kunieda, and T. Ooi J. Am. Chem. Soc. 135 2013 590 593
16. M. Prat, J. Ribas, and M. Moreno-Mañas Tetrahedron 48 1992 1695 1706
17. M. Moreno-Mañas, F. Pajuelo, T. Parella, and R. Pleixats Organometallics 16 1997 205 209
18. V. Branchadell, M. Moreno-Mañas, F. Pajuelo, and R. Pleixats Organometallics 18 1999 4934 4941
19. F. Delbecq, and C. Lepouge Organometallics 19 2000 2716 2723
20. S. Norsikian, and C.-W. Chang Curr. Org. Synth. 6 2009 264 289
21. B.M. Trost, and T.R. Verhoeven J. Am. Chem. Soc. 99 1977 3867 3868
22. M. Ahmar, B. Cazes, and J. Goré Tetrahedron 43 1987 3453 3463
23. B.M. Trost Angew. Chem., Int. Ed. Engl. 28 1989 1173 1192
24. A. Tenaglia, and F. Kammerer Synlett 1996 576 578
25. Transition metal catalysed enantioselective allylic substitution in organic synthesis U. Kazmaier Top. Organomet. Chem. Vol. 38 2012 Springer Berlin, Heidelberg, Germany 345
26. S. Inuki Total Synthesis of Bioactive Natural Product by Palladium-catalyzed Domino Cyclization of Allenes and Related Compounds 2012 Springer Theses
27. K.C. Majumdar, B. Chattopadhyay, P.K. Maji, S.K. Chattopadhyay, and S. Samanta Heterocycles 81 2010 795 866
28. J.E. Baldwin J. Chem. Soc., Chem. Commun. 1976 734 736
29. J.E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman, and R.C. Thomas J. Chem. Soc., Chem. Commun. 1976 736 738
30. J.E. Baldwin J. Chem. Soc., Chem. Commun. 1976 738 741
31. See also a recent discussion: I.V. Alabugin, K. Gilmore, and M. Manoharan J. Am. Chem. Soc. 133 2011 12608 12623
32. M. Daly, A.A. Cant, L.S. Fowler, G.L. Simpson, M. Hans, and A. Sutherland J. Org. Chem. 77 2012 10001 10009
33. H. Yao, J. Ren, and R. Tong Chem. Commun. 2013 193 195
34. M. Zucco, F. Le Bideau, and M. Malacria Tetrahedron Lett. 36 1995 2487 2490
35. S. Monfette, and D.E. Fogg Chem. Rev. 109 2009 3783 3816
36. J. Prunet Eur. J. Org. Chem. 20 2011 3634 3647
37. L.H. Peeck, R.D. Savka, and H. Plenio Chem. - Eur. J. 18 2012 12845 12853
38. T. Hirao, J. Enda, Y. Ohshiro, and T. Agawa Tetrahedron Lett. 22 1981 3079 3080
39. B.M. Trost, and C.R. Self J. Am. Chem. Soc. 105 1983 5942 5944
40. B.M. Trost, and A. Brandi J. Org. Chem. 49 1984 4811 4816
41. T. Otha, T. Hosokawa, S.-I. Murahashi, K. Miki, and N. Kasai Organometallics 4 1985 2080 2085
42. J. Tsuji, M. Yuhara, M. Minato, H. Yamada, F. Sato, and Y. Kobayashi Tetrahedron Lett. 29 1988 343 346
43. H. Inami, T. Ito, H. Urabe, and F. Sato Tetrahedron Lett. 34 1993 5919 5922
44. R. Schobert, and B. Barnickel Synthesis 2009 2778 2784 For theoretical approaches see
45. V. Branchadell, M. Moreno-Mañas, and R. Pleixats Organometallics 21 2002 2407 2412 For a review on the interaction between β-substituents (including silicon groups) and the allyl moiety of palladium complexes, see
46. K.J. Szabó Chem. Soc. Rev. 30 2001 136 143
47. S. Thorimbert, and M. Malacria Tetrahedron Lett. 37 1996 8483 8486
48. C. Commandeur, S. Thorimbert, and M. Malacria J. Org. Chem. 68 2003 5588 5592
49. V. Branchadell, M. Moreno-Mañas, R. Pleixats, S. Thorimbert, C. Commandeur, C. Boglio, and M. Malacria J. Organomet. Chem. 687 2003 337 345
50. S. Thorimbert, C. Taillier, S. Bareyt, D. Humilière, and M. Malacria Tetrahedron Lett. 45 2004 9123 9126
51. C. Boglio, S. Stahlke, S. Thorimbert, and M. Malacria Org. Lett. 7 2005 4851 4854
52. M.-C. Lamas, M. Malacria, and S. Thorimbert Eur. J. Org. Chem. 2011 2777 2780
53. S. Thorimbert, and M. Malacria Tetrahedron Lett. 39 1998 9659 9660
54. G. Poli, G. Giambastiani, M. Malacria, and S. Thorimbert Tetrahedron Lett. 42 2001 6287 6289
55. S. Thorimbert, G. Giambastiani, C. Commandeur, M. Vitale, G. Poli, and M. Malacria Eur. J. Org. Chem. 2003 2702 2708
56. H. Boehme, and L. Haefner Chem. Ber. 99 1966 879 884
57. D. Brillon Synth. Commun. 16 1986 291 298
58. G. Cravotto, G.B. Giovenzana, M. Sisti, and G. Palmisano Tetrahedron 54 1998 1639 1646
59. J.L. Speier, J.A. Webster, and G.H. Barnes J. Am. Chem. Soc. 79 1957 974 979 For some recent studies see
60. J. Li, J.M. Suh, and E. Chin Org. Lett. 12 2010 4712 4715
61. Y. Kawasaki, Y. Ishikawa, K. Igawa, and K. Tomooka J. Am. Chem. Soc. 133 2011 20712 20715
62. D.A. Rooke, and E.M. Ferreira Angew. Chem., Int. Ed. 51 2012 3225 3230
63. H. Kinoshita, H. Shinokubo, and K. Oshima Org. Lett. 6 2004 4085 4088
64. I. Usui, S. Schmidt, M. Keller, and B. Breit Org. Lett. 10 2008 1207 1210
65. R. Gosh, and A. Sarkar J. Org. Chem. 76 2011 8508 8512
66. B. Salem, and J. Suffert Angew. Chem., Int. Ed. 43 2004 2826 2830
67. C. Bour, G. Blond, B. Salem, and J. Suffert Tetrahedron 62 2006 10567 10581 See also two recent reviews dealing with electrocyclizations
68. C.M. Beaudry, J.P. Malerich, and D. Trauner Chem. Rev. 105 2005 4757 4778
69. S. Thompson, A.C. Coyne, P.C. Knipe, and M.D. Smith Chem. Soc. Rev. 40 2011 4217 4231
70. D. Brillon, and P. Deslongchamps Can. J. Chem. 65 1987 43 45
71. D. Brillon, and P. Deslongchamps Can. J. Chem. 65 1987 56 68 see also
72. C.J. Burns, M. Gill, and S. Saubern Aust. J. Chem. 50 1997 1067 1080
73. C. Mukai, N. Kuroda, R. Ukon, and R. Itoh J. Org. Chem. 70 2005 6282 6290
74. T. Kawamura, F. Inagaki, S. Narita, Y. Takahashi, S. Hirata, S. Kitagaki, and C. Mukai Chem. - Eur. J. 16 2010 5173 5183
75. 2 led to 21 in a moderate 58% yield K. Chandra, P. Saravanan, and V.K. Singh Tetrahedron Lett. 42 2001 5309 5311