Expanding the scope of Enantioselective FerroPHANE-promoted [3+2] annulations with α,β-unsaturated ketones

Chemistry - A European Journal

Volumn 16, Issue 3, 2010, Pages 1033-1045

  Pinto, Nathalie ^a   Neel, Mathilde ^a   Panossian, Armen ^a   Retailleau, Pascal ^a   Gilles Frison, ^b   Voituriez, Arnaud ^a   Marinetti, Angela ^a  

^a CNRS   (France)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

Allenyl phosphonates; Cyclization; Enantioselectivity; Organocatalysis; Spiro compounds

Indexed keywords

ALLENYL; CHIRAL CATALYST; CHIRAL INDUCTION; CYCLISATIONS; CYCLOPENTENES; DFT METHOD; ENANTIOSELECTIVE; FERROCENOPHANES; ORGANOCATALYSIS; ORGANOCATALYSTS; PHOSPHONATES; SPIRO COMPOUNDS; UNSATURATED KETONES;

CATALYSIS; CATALYSTS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; ESTERS; ISOMERS; KETONES; PHOSPHORUS COMPOUNDS; RATE CONSTANTS; REACTION KINETICS;

CYCLIZATION;

FERROUS ION; KETONE; PHOSPHINE; PHOSPHINE DERIVATIVE; PHOSPHINIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; FERROUS COMPOUNDS; KETONES; MOLECULAR CONFORMATION; PHOSPHINES; PHOSPHINIC ACIDS; STEREOISOMERISM;

EID: 75249107949     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901893     Document Type: Article

References (94)

1. a) D.H. Valentine, J. H. Hillhouse, Synthesis, 2003, 317;
2. b) J. L. Methot, W.R. Roush, Adv. Synth. Catal. 2004, 346, 1035;
3. c) J. L. Methot, W.R. Roush in Science of Synthesis, Vol. 42.11, (Ed.: F. Mathey), Thieme, Stuttgart, 2008, p. 469.
4. For reviews, see:
5. a) X. Lu, C. Zhang, Z. Xu, Acc. Chem. Res. 2001, 34, 535;
6. b)L.-W. Ye, J. Zhou, Y. Tang, Chem. Soc. Rev. 2008, 37,
7. . For relevant examples, see :
8. c) Z. Xu, X. Lu, J. Org. Chem. 1998, 63, 5031;
9. d) Z. Xu, X. Lu, Tetrahedron Lett. 1999, 40, 549;
10. e) X-F. Zhu, J. Lan, O. Kwon, J. Am. Chem. Soc. 2003, 125, 4716;
11. f) B. Zhang, Z. He, S. Xu, G. Wu, Z. He, Tetrahedron, 2008, 64, 9471;
12. g)G.-L. Zhao, M. Shi, J. Org. Chem. 2005, 70, 9975;
13. h) Y. Du, X. Lu, Y. Yu, J. Org. Chem. 2002, 67, 8901;
14. i) J. L. Garcia Ruano, A. Núñez, Jr., M. R. Martín, A. Fraile, J. Org. Chem. 2008, 73, 9366;
15. j) X.-Y. Guan, M. Shi, J. Org. Chem. 2009, 74, 1977;
16. k) R. A. Jones, M. J. Krische, Org. Lett. 2009, 11, 1849;
17. l) J.-C. Wang, M. J. Krische, Angew. Chem. 2003, 115, 6035; Angew. Chem. Int. Ed. 2003, 42, 5855;
18. m)K. Kumar, A. Kapur, P.S. Ishar, Org. Lett. 2000, 2, 787;
19. n) X. Lu, Z. Lu, X. Zhang, Tetrahedron, 2006, 62, 457;
20. o) C. E. Henry, O. Kwon, Org. Lett. 2007, 9, 3069; p) T. Q. Pham, S. G. Pyne, B. W. Skelton, A. H. White, J. Org. Chem., 2005, 70, 6369;
21. q) Y. Du, X. Lu, J. Org. Chem. 2003, 68, 6463;
22. r) S. G. Pyne, K. Schafer, B. W. Skelton, A. H. White, Chem. Commun. 1997, 2267.
23. a) G. Buono, O. Chiodi, M. Wills, Synlett, 1999, 377;
24. b) H. Gröger, E. Burda in Phosphorus Ligands in Asymmetric Catalysis, Vol. 3, (Ed. : A. Börner), Wiley-VCH, Weinheim, 2008, p. 1175.
25. E. Vedejs, O. Daugulis, S. T. Diver, J. Org. Chem. 1996, 61, 430.
26. G. Zhu, Z. Chen, Q. Jiang, D. Xiao, P. Cao, X. Zhang, J. Am. Chem. Soc. 1997, 119, 3836.
27. a) R. P. Wurz, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 12234;
28. b) J. E.
29. Wilson, G. C. Fu, Angew. Chem. 2006, 118, 1454; Angew. Chem. Int. Ed. 2006, 45, 1426;
30. c) Y.-Q. Jiang, Y.-L. Shi, M. Shi, J. Am. Chem. Soc. 2008, 130, 7202;
31. d) Y.-K. Chung, G. C. Fu, Angew. Chem., 2009, 121, 2259;
32. Angew. Chem. Int. Ed. 2009, 48, 2225;
33. e) D.J. Wallace, R. L. Sidda, R. A. Reamer, J. Org. Chem. 2007, 72, 1051.
34. a) E. Vedejs, O. Daugulis, J. Am. Chem. Soc. 1999, 121, 5813;
35. b) S. A. Shaw, P. Aleman, E. Vedejs, J. Am. Chem. Soc. 2003, 125, 13368;
36. c) M. Shi, L.-H. Chen, C.-Q. Li, J. Am. Chem. Soc. 2005, 127, 3790;
37. d) B. J. Cowen, S. J. Miller, J. Am. Chem. Soc. 2007, 129, 10988;
38. e) Y.-Q. Fang, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 5660;
39. f) Z. Chen, G. Zhu, Q. Jiang, D. Xiao, P. Cao, X. Zhang, J. Org. Chem. 1998, 63, 5631;
40. g) M. Shi, L.-H. Chen, Chem. Commun. 2003, 1310;
41. h) M. Shi, G.-N. Ma, J. Gao, J. Org. Chem. 2007, 72, 9779;
42. i) K. Matsui, S. Takizawa, H. Sasai, Synlett, 2006, 761.
43. a) L. Jean, A. Marinetti, Tetrahedron Lett. 2006, 47, 2141;
44. b) N. Fleury-Brégeot, L. Jean, P. Retailleau, A. Marinetti, Tetrahedron, 2007, 63, 11920;
45. c) A. Panossian, N. Fleury-Brégeot, A. Marinetti, Eur. J. Org. Chem. 2008, 3826;
46. d) N. Pinto, N. Fleury-Brégeot, A. Marinetti, Eur. J. Org. Chem. 2009, 146.
47. a) A. Voituriez, A. Panossian, N. Fleury-Brégeot, P. Retailleau, A. Marinetti, J. Am. Chem. Soc. 2008, 130, 14030;
48. b) A. Voituriez, A. Panossian, N. Fleury-Brégeot, P. Retailleau, A. Marinetti, Adv. Synth Catal, 2009, 351, 1968.
49. a) P. Savignac, B. lorga, Modern Phosphonate Chemistry, CRC Press, Boca Raton, 2003;
50. b) F. Palacios, C. Alonso, J. M. de Los Santos, Chem. Rev. 2005, 105, 899;
51. c) J.-A. Ma, Chem. Soc. Rev., 2006, 35, 630.
52. a) M. Hanedanian, O. Loreau, F. Taran, C. Mioskowski, Tetrahedron Lett. 2004, 45, 7035;
53. b) D. Leclercé, M. Sawicki, F. Taran, Org. Lett. 2006, 8, 4283;
54. c) H. Park, C.-W. Cho, M.J. Krische, J. Org. Chem. 2006, 71, 7892;
55. d) Y. Lin, D. Bernardi, E. Doris, F. Taran, Synlett, 2009, 1466.
56. For related examples of aminocatalysis see:
57. a) S. Samanta, C.-G. Zhao, J. Am. Chem. Soc. 2006, 128, 7442;
58. b) D. Pettersen, M. Mar colini, L. Bernardi, F. Fini, R. P. Herrera, V. Sgarzani, A. Ricci, J. Org. Chem. 2006, 71, 6269;
59. c) S. Sulzer-Mossé, M. A. Tissot, A. , Org. Lett. 2007, 9, 3749;
60. d) J. Wang, L. D. Heikkinen, H. Li, L. Zu, W. Jiang, H. Xie, W. Wang, Adv. Synth. Catal. 2007, 349, 1052;
61. e) M. Capuzzi, D. Perdicchia, K. A. Jorgensen, Chem. Eur. J. 2008, 14, 128.
62. a) V. Mark, Tetrahedron Lett. 1962, 3, 281;
63. b) R. S. Macomber, E. R. Kennedy, J. Org. Chem. 1976, 41, 3191;
64. c) B. Iorga, F. Eymery, D. Carmichael, P. Savignac, Eur. J. Org. Chem. 2000, 3103.
65. a) C. Zhang, X. Lu, J. Org. Chem. 1995, 60, 2906;
66. b) T. Dudding, O. Kwon, E. Mercier, Org. Lett. 2006, 8, 3643;
67. c) Y. Liang, S. Liu, Y. Xia, Y. Li, Z.-X. Yu, Chem. Eur. J. 2008, 14, 4361.
68. Isomerization of 2,3-butadienylphosphonates into the corresponding alkynes is known to take place in the presence of strong bases: G. Sturtz, Bull. Soc. Chim. Fr. 1967, 134.
69. For related phosphine promoted isomerizations of acetylenic esters into dienes, see:
70. a) B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933;
71. b) C. Guo, X. Lu, J. Chem. Soc. Perkin Trans. 1, 1993, 1921;
72. c) S. D. Rychnovsky, J. Kim, J. Org. Chem. 1994, 59, 2659.
73. a) V. M. Dembitsky, A. Al Quntar, A. Haj-Yehia, M. Srebnik, Mini- Rev. Org. Chem. 2005, 2, 91;
74. b) T. Minami, J. Motoyoshiya, Synthesis, 1992 333.
75. The minor regioisomer has not been unambiguously characterized.
76. According to ref. 6b, the same compound can be obtained in 75 % yield and 89 % ee, by using tBu-Binepine as the catalyst.
77. The same substrate was reported to undergo regioselective cyclization in the presence of tBu-Binepineas the catalyst (68% yield, 73% ee): see reference [6b].
78. As a control experiment, the same reaction has been performed in the presence of a catalytic amount of triphenylphosphine. The reaction afforded 7j in 74% yield,with a diastereoisomers ratio of 42:58.
79. a) E. Mercier, B. Fonovic, C. Henry, O. Kwon, T.Dudding, Tetrahedron Lett. 2007, 48, 3617;
80. b) Y. Xia, Y. Liang, Y. Chen, M. Wang, L. Jiao, F. Huang,S. Liu, Y. Li, Z.-X. Yu, J. Am. Chem. Soc. 2007, 129, 3470.
81. Stereochemical control at a later step of the catalytic cycle cannot be ruled out either.
82. A stable tetravalent enolate zwitterions displaying P + O interaction has been isolated by Kwon: X.-F. Zhu, C. Henry, O. Kwon, J. Am. Chem. Soc. 2007, 129, 6722.
83. a) S. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200;
84. b) J. P. Perdew, Phys. Rev. B, 1986, 33, 8822;
85. c) A. D. Becke, Phys. Rev. A, 1988, 38, 3098.
86. M. Sierka, A. Hogekamp, R. Ahlrichs, J. Chem. Phys. 2003, 118, 9136.
87. R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 162, 165.
88. a) A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571;
89. b) F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297.
90. F. Weigend, Phys. Chem. Chem. Phys. 2006, 8, 1057.
91. COLLECT, data collection software, B. V. Nonius, 1999 .
92. Z. Otwinowski, W. Minor, Methods in Enzymology, Vol. 276, Macro- molecular Crystallography, Part A, (Ed. : C. W. Carter, Jr., R. M. Sweet), Academic Press, New York, 1997, pp. 307-326, .
93. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giaco- vazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
94. G. M. Sheldrick, Acta Crystallogr. Sect. A, 2008, 64, 112.