Enantioselective organocatalytic domino oxa-michael/aldol/ hemiacetalization: Synthesis of polysubstituted furofuranes containing four stereocenters

Angewandte Chemie - International Edition

Volumn 48, Issue 31, 2009, Pages 5701-5704

  Reyes, Efraím ^a   Talavera, Garazi ^a   Vicario, Jose L ^a   Badia, Dolores ^a   Carrillo, Luisa ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Asymmetric catalysis; Domino reactions; Heterocycles; Organocatalysis; Oxa Michael reaction

Indexed keywords

ASYMMETRIC CATALYSIS; DOMINO REACTIONS; HETEROCYCLES; ORGANOCATALYSIS; OXA-MICHAEL REACTION;

ADDITION REACTIONS; ALDEHYDES; AMINES; ENANTIOSELECTIVITY; RATE CONSTANTS; REACTION KINETICS;

CATALYSIS;

EID: 70349897776     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200901333     Document Type: Article

References (49)

1. For some selected reviews, see: a) N. Ismabery, R. Lavila, Chem. Eur. J. 2008, 14, 8444;
2. b) C. J. Chapman, C. G. Frost, Synthesis 2007, 1;
3. c) H. Miyabe, Y. Takemoto, Chem. Eur. J. 2007, 13, 7280;
4. d) N. T. Patil, Y. Yamamoto, Synlett 2007, 1994;
5. e) Multicomponent Reactions (Eds.: J. Zhu, H. Bienayme), Wiley-VCH, Weinheim, 2005;
6. f) D. Tejedor, F. Garcia-Tellado, Chem. Soc. Rev. 2007, 36, 484;
7. g) L. F. Tietze, G. Brasche, K. Gerike, Domino Reactions in Organic Chemistry, Wiley-VCH, Weinheim, 2006;
8. h) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292;
9. Angew. Chem. Int. Ed. 2006, 45, 7134;
10. i) A. Dömling, Chem. Rev. 2006, 106, 17;
11. j) H.-C. Guo, J.-A. Ma, Angew. Chem. 2006, 118, 362;
12. Angew. Chem. Int. Ed. 2006, 45, 354;
13. k) D. J. Ramon, M. Yus, Angew. Chem. 2005, 117, 1628;
14. Angew. Chem. Int. Ed. 2005, 44, 1602.
15. For two pioneering reports, see: a) M. Marigo, T. Schulte, J. Franzén, K. A. Jorgensen, J. Am. Chem. Soc. 2005, 127, 15710;
16. b) Y. Huang, A. M. Walji, C. H. Larsen, D. W C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15051.
17. For general reviews on organocatalytic cascade reactions, see: c) X. Yu, W. Wang, Org. Biomol. Chem. 2008, 6, 2037;
18. d) D. Enders, C. Grondal, M. R. M. Huettl, Angew. Chem. 2007, 119, 1590;
19. Angew. Chem. Int. Ed. 2007, 46, 1570;
20. e) G. Guillena, D. J. Ramon, M. Yus, Tetrahedron: Asymmetry 2007, 18, 693.
21. For some selected general reviews on asymmetric organocatalysis, see: a) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232;
22. Angew. Chem. Int. Ed. 2008, 47, 6138;
23. b) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
24. Angew. Chem. Int. Ed. 2008, 47, 4638;
25. c) special issue on organocatalysis Chem. Rev. 2007, 107(12);
26. d) B. List, J.-W. Yang, Science 2006, 313, 1584.
27. a) J. L. Vicario, D. Badía, L. Carrillo, Synthesis 2007, 2065;
28. b) D. Almaçi, D. A. Alonso, C. Najera, Tetrahedron: Asymmetry 2007, 18, 299;
29. c) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701;
30. d) S. Sulzer-Mossé, A. Alexakis, Chem. Commun. 2007, 3123.
31. a values of 16 and 17: D. A. Alonso, S. Kitagaki, N. Utsumi, C. F. Barbas III, Angew. Chem. 2008, 120, 4664;
32. Angew. Chem. Int. Ed. 2008, 47, 4588.
33. a) T. Govender, L. Hojabri, F. M. Moghaddam, P. I. Arvidsson, Tetrahedron: Asymmetry 2006, 17, 1763;
34. b) H. Sunden, I. Ibrahem, G.-L. Zhao, L. Eriksson, A. Cordova, Chem. Eur. J. 2007, 13, 574;
35. c) A. Merschaert, P. Delbeke, D. Daloze, G. Dive, Tetrahedron Lett. 2004, 45, 4697;
36. d) H. Li, J. Wang, T. E-Nunu, L. Zu, W. Jiang, S. Wei, W. Wang, Chem. Commun. 2007, 507;
37. e) M. M. Biddle, M. Lin, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 3830.
38. See also f) D. R. Li, A. Murugan, J. R. Falck, J. Am. Chem. Soc. 2008, 130, 46;
39. g) T. Tanaka, T. Kumamoto, T. Ishikawa, Tetrahedron: Asymmetry 2000, 11, 4633.
40. a) S. Bertelsen, P. Diner, R. L. Johansen, K. A. Jorgensen, J. Am. Chem. Soc. 2007, 129, 1536.
41. For a similar reaction using enones as Michael acceptors, see: b) A. Carlone, G. Bartoli, M. Bosco, F. Pesciaioli, P. Ricci, L. Sambri, P. Melchiorre, Eur. J. Org. Chem. 2007, 5492.
42. a) C. M. Reisinger, X. Wang, B. List, Angew. Chem. 2008, 120, 8232;
43. Angew. Chem. Int. Ed. 2008, 47, 8112;
44. b) X. Lu, Y. Liu, B. Sun, B. Cindric, L. Deng, J. Am. Chem. Soc. 2008, 130, 8134.
45. For an earlier example of an attempted amine-catalyzed conjugate addition of alcohols to enals furnishing low levels of enantioselection, see: a) D. Díez, M. G. Nuñez, A. Benéitez, R. F. Moro, I. S. Marcos, P. Basabe, H. B. Broughton, J. G. Urones, Synlett 2009, 390;
46. b) T. Kano, Y. Tanaka, K. Maruoka, Tetrahedron 2007, 63, 8658.
47. The absolute configuration of the compounds 4 was assigned by analogy from the X-ray analysis of the corresponding O-acetyl p-chlorobenzoyl derivative of 4 b (see the Supporting Information). CCDC 723339 contains the supplementary crystallo-graphic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
48. We also think that it is the dihydroxyacetone dimer 2 itself which acts as the oxygen nucleophile because reactions in solvents having the ability to retrodimerize 2, such as MeOH or THF, proceeded with very low conversions.
49. The reaction of crotonaldehyde with hydroxyacetophenone under the optimized reaction conditions did not furnish any product; only unmodified starting materials were recovered.