Enantioselective synthesis of cyclopentene carbaldehydes by a direct multicatalytic cascade sequence: Carbocyclization of aldehydes with alkynes

Chemistry - A European Journal

Volumn 16, Issue 6, 2010, Pages 1750-1753

  Jensen, Kim L ^a   Franke, Patrick T ^a   Arróniz, Carlos ^a   Kobbelgaard, Sara ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Aldehydes; Cascade reactions; Cyclopentenes; Lewis acid; Organocatalysis

Indexed keywords

BUILDING BLOCKES; CARBOCYCLIZATION; CASCADE REACTIONS; CYCLOPENTENE CARBALDEHYDES; CYCLOPENTENES; DIASTEREOSELECTIVE; DRIVING FORCES; ENAMINES; ENANTIO; ENANTIOSELECTIVE SYNTHESIS; GOOD YIELD; IMINIUM; INERT ATMOSPHERES; LEWIS ACID; MALONONITRILES; MOLECULAR FRAMEWORKS; ORGANOCATALYSIS; SIGMATROPIC REARRANGEMENTS; TANDEM REACTION; TOTAL SYNTHESIS; UNSATURATED ALDEHYDES;

ACETYLENE; ACIDS; BIOLOGICAL SYSTEMS; CATALYSIS; COMPLEXATION; NUCLEOPHILES; RATE CONSTANTS; REACTION KINETICS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ALDEHYDES;

ALDEHYDE; ALKYNE; CYCLOPENTANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKYNES; CATALYSIS; CYCLIZATION; CYCLOPENTANES; STEREOISOMERISM;

EID: 75749120984     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903405     Document Type: Article

References (74)

1. K.C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118. 7292;
2. Angew. Chem. Int. Ed. 2006, 45, 7134.
3. a) D. Enders, C. Grondai. M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590;
4. Angew. Chem. Int. Ed. 2007, 46, 1570;
5. b) A. M. Walji. D. W. C MacMillan, Synlett 2007, 1477:
6. (c) Y. Xinhong, W. Wang, Org. Biomol. Chem. 2008, 6, 2037:
7. (d) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
8. Angew. Chem. Int. Ed. 2008, 47, 4638.
9. For examples on cascade catalysis, see: a) Y. Huang. A.M. Walji, C. H. Larsen, D. W. C. MacMillan. J. Am. Chem. Soc. 2005, 127, 15051:
10. b) A. Carlone, S. Cabrera. M. Mango. K. A. Jørgensen, Angew. Chem. 2007, 119, 1119;
11. Angew. Chem. Int. Ed. 2007, 46, 1101:
12. (c) Y. Hayashi, H. Goloh, R. Masui, H. Ishikawa, Angew. Chem. 2008, 120, 4076;
13. Angew. Chem. Int. Ed. 2008, 47, 4012;
14. (d) D. Enders. C. Wang. J. W. Bats, Angew. Chem. 2008, 120, 7649:
15. Angew. Chem. Int. Ed. 2008, 47. 7539:
16. e) C. Chandler. P. Galzerano, A. Michrowska, B. List. Angew. Chem. 2009, 121, 2012:
17. Angew. Chem. Int. Ed. 2009, 48, 1978;
18. f) L. Zu, S. Zhang, H. Xie, W. Wang, Org. Lett. 2009, 48, 1627;
19. g) M. Rueping, A. Kuenkel. F. Tato. J. W. Bats, Angew. Chem. 2009, 121, 3754;
20. Angew. Chem. Int. Ed. 2009, 48, 3699;
21. h) L.-Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7332;
22. Angew. Chem. Int. Ed. 2009, 48, 7196.
23. For reviews, see: a) A. Duschek, S. F. Kirsch. Angew. Chem. 2008, 120, 5787;
24. Angew. Chem. Int. Ed. 2008. 47, 5703;
25. b) Z. Shao. H. Zhang, Chem. Soc. Rev. 2009, 38, 2745: for recent examples, see:
26. (c) Y. Chi. S. T. Scroggins. J. M. J. Fréchet, J. Am Chem. Soc. 2008, 130, 6322:
27. (d) B. Simmons, A. M. Walji, D. W. C MacMillan, Angew. Chem. 2009, 121, 4413;
28. Angew. Chem. Int. Ed. 2009, 48, 4349;
29. e) S. P. Lalhrop, T. Rovis, J. Am. Chem. Soc. 2009, 131, 13628.
30. a) C. Nevado, D. J. Cárdenas, A. M. Echavarren. Chem. Eur. J. 2003, 9, 2627:
31. b) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064;
32. Angew. Chem. Int. Ed. 2006, 45, 7896;
33. (c) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395;
34. (d) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180:
35. e) A. Fürstner. P. W. Davies. Angew. Chem. 2007 119, 3478;
36. Angew. Chem. Int. Ed. 2007, 46, 3410.
37. For examples with preformed enamines, see: a) T. J. Harrison. G. R. Dake, Org. Lett. 2004, 6, 5023:
38. b) T. J. Harrison, B. O. Patrick. G. R. Dake. Org. Lett. 2007, 9, 367: for examples with catalytically generated enamines. see:
39. (c) I. lbrahem, A. Cúrdova, Angew. Chem. 2006, 118, 1986;
40. Angew. Chem. Int. Ed. 2006, 45, 1952:
41. (d) Q. Ding, J. Wu. Org. Lett. 2007, 9, 4959:
42. e) J. T. Binder, B. Crone, T. T. Haug, H. Menz, S. F. Kirsch, Org. Lett. 2008, 10, 1025 and references cited therein.
43. a) M. Nakoji, T. Kanayama, T. Okino. Y. Takemoto, Org. Lett. 2001, 3, 3329;
44. b) G. Chen, Y. Deng, L. Gong, A. Mi, X. Cui. Y. Jiang. M. C. K. Choi, A. S. C. Chan, Tetrahedron: Asymmetry 2001, 12, 1567:
45. (c) M. Nakoji, T. Kanayama, T. Okino, Y. Takemoto. J. Org. Chem. 2002, 67, 7418;
46. T. Kanayama, K. Yoshida, H. Miyabe. Y. Takemoto, Angew. Chem. 2003, 115, 2100;
47. Angew. Chem. Int. Ed. 2003, 42, 2054:
48. e) B.G. Jellerichs, J.-R. Kong, M.J. Krische. J. Am. Chem. Soc. 2003, 125, 7758;
49. f) V. Komanduri, M.J. Krische, J. Am. Chem. Soc. 2006, 128, 16448;
50. g)S. Chercheja. P. Eilbracht, Adv. Synth. Catal. 2007, 349, 1897;
51. h) M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem. 2007, 119, 7027;
52. Angew. Chem. Int. Ed. 2007, 46, 6903:
53. (i) S. Mukherjee. B. List, J. Am. Chem. Soc. 2007, 129, 11336:
54. j) W. Hu, X. Xu, J.. Zhou. W.-J. Liu. H. Huang. J. Hu. L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 7782:
55. k) K. Sorimachi. M. Terada, J. Am. Chem. Soc. 2008, 130, 14452;
56. H.-F. Wang, T. Yang. P-F. Xu, D. J. Dixon, Chem. Commun. 2009, 3916:
57. (m) M. Terada. Y. Toda, J. Am. Chem. Soc. 2009, 131, 6354:
58. n) T. Yang, A. Ferrali, F. Sladojevich, L. Campbell. D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 9140:
59. o) S. Chercheja. T. Rothenbücher. P. Eilbracht. Adv. Synth. Catal. 2009, 351, 339.
60. T. Yang, A. Ferrali, L. Campbell. D. J. Dixon, Chem. Commun. 2008, 2923.
61. During the preparation of this manuscript, a paper describing an enantioselective one-pot organocatalytic Michael addition/gold-catalyzed tandem acetalization/cyclization appeared, see: S. Belot, K. A. Vogt. C. Besnard, N. Krause, A. Alexakis. Angew. Chem. 2009, 121, 9085:
62. Angew. Chem. Int. Ed. 2009, 48, 8923.
63. a) M. Lorenz. W. Boland, K. Dettner. Angew. Chem. 1993, 105, 904:
64. Angew. Chem. Int. Ed. Engl. 1993, 32, 912;
65. b) A. Nangia, G. Prasuna. P. B. Rao, Tetrahedron 1997, 53, 14507;
66. (c) D. E. Chavez. E. N. Jacobsen. Org. Lett. 2003, 5, 2563;
67. (d) N. A. Petasis, M. A. Patane. Tetrahedron 1992, 48, 5757:
68. e) D. R. Williams, L. A. Robinson, C. R. Nevili, J. P. Reddy, Angew. Chem. 2007, 119, 933;
69. Angew. Chem. Int. Ed. 2007, 46, 915.
70. F. H. Jardine, L. Rule, A. G. Vohra. J. Chem. Soc. A 1970, 238.
71. The diastereomeric ratio was determined by 1H NMR spectroscopy on the crude reaction mixture.
72. CCDC-749346 contains the supplementary crystallography data. These data can be obtained free of charge from The Cambridge Crystallography Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
73. Note added in proof: After the acceptance of this manuscript, a related paper based on kinetic asymmetric transformation (DYKAT) for the same reaction was published in this journal, see:
74. G-L. Zhao. F. Ullah. L. Deiana, S. Lin, Q. Zhang. J. Sun. I. Ibrahem, P. Dziedzic. A. Cordova, Chem. Eur. J. 2010, 16, 1585.