Organocatalytic highly enantioselective α-arylation of β-ketoesters

Angewandte Chemie - International Edition

Volumn 46, Issue 29, 2007, Pages 5515-5519

  Alemán, José ^a   Richter, Bo ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

arylation; ketoesters; Organocatalysis; Quinine; Quinones

Indexed keywords

CATALYSTS; ELECTRONS; KETONES;

Α-ARYLATION; Β-KETOESTERS; ORGANOCATALYSIS; QUININE; QUINONES;

ESTERS;

EID: 34547184381     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701009     Document Type: Article

References (45)

1. For reviews on organocatalysis, see, for example: a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840;
2. Angew. Chem. Int. Ed. 2001, 40, 3726;
3. b) E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481;
4. c) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
5. Angew. Chem. Int. Ed. 2004, 43, 5138;
6. d) Acc. Chem. Res. 2004, 37(8) special issue on organocatalysis;
7. e) A. Berkessel, H. Gröger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005;
8. f) J. Seayad, B. List, Org. Biomol. Chem. 2005, 3, 719;
9. g) M. J. Gaunt, C. C. C. Johansson, A. McNally, N. T. Vo, Drug Discovery Today 2007, 12, 8;
10. h) P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007.
11. a) M. B. Smith, J. March, Advanced Organic Chemistry, 5th ed., Wiley-Interscience, New York, 2001, chap. 13, p. 850;
12. b) E. Buncel, J. M. Dust, F. Terrier, Chem. Rev. 1995, 95, 2261.
13. See, for example: a) N. Selvakumar, B. Yadi Reddy, G. Sunil Kumar, J. Iqbal, Tetrahedron Lett. 2001, 42, 8395;
14. b) R. J. Snow, T. Butz, A. Hammach, S. Kapadia, T. M. Morowick, A. S. Prokopowicz, H. Takahashi, J. D. Tan, M. A. Tschantz, X.-J. Wang, Tetrahedron 2002, 58, 7553;
15. c) N. J. Lawrence, C. A. Davies, M. Gray, Org. Lett. 2004, 6, 4957.
16. a) M. Bella, S. Kobbelgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 3670;
17. b) S. Kobbelgaard, M. Bella, K. A. Jørgensen, J. Org. Chem. 2006, 71, 4980.
18. See for example, a) V. K. Tandon, R. B. Chhor, R. V. Singh, S. Rai, D. B. Yadav, Bioorg. Med. Chem. Lett. 2004, 14, 1079;
19. b) V. K. Tandon, D. B. Yadav, R. V. Singh, A. K. Chaturvedi, P. K. Shukla, Bioorg. Med. Chem. Lett. 2005, 15, 5324, and references therein;
20. c) for regioselective additions to juglones, see: S. Laugraud, A. Guigant, C. Chassangard, J. d'Angelo, J. Org. Chem. 1988, 53, 1557.
21. a) The Chemistry of the Quinoid Compounds (Eds: S. Patai, Z. Rapoport), Wiley, New York, 1988;
22. b) for a review of quinone chemistry, see: A. Kutyrev, Tetrahedron 1991, 47, 8043.
23. See: a) J. Christoffers, A. Mann, Eur. J. Org. Chem. 1999, 1259;
24. b) J. Comelles, M. Moreno-Mañas, E. Pérez, A. Roglans, R. M. Sebastián, A. Vallribera, J. Org. Chem. 2004, 69, 6834.
25. For recent examples of organocatalyzed quinine reactions, see, for example: a) G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, P. Melchiorre, L. Sambri, Angew. Chem. 2005, 117, 6375;
26. Angew. Chem. Int. Ed. 2005, 44, 6219;
27. b) S. H. McCooey, S. J. Connon, Angew. Chem. 2005, 117, 6525;
28. Angew. Chem. Int. Ed. 2005, 44, 6367;
29. c) T. B. Poulsen, C. Alemparte, S. Saaby, M. Bella, K. A. Jørgensen, Angew. Chem. 2005, 117, 2956;
30. Angew. Chem. Int. Ed. 2005, 44, 2896;
31. d) H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. 2005, 117, 107;
32. Angew. Chem. Int. Ed. 2005, 44, 105;
33. e) S. Lou, B. M. Toaa, A. Ting, S. E. Schaus, J. Am. Chem. Soc. 2005, 127, 11256;
34. f) H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948;
35. g) Y. Wang, X Liu, L. Deng, J. Am. Chem. Soc. 2006, 128, 3928;
36. h) J. Song, J. Wang, H. Li, L. Zu, W. Jiang, H. Xie, W. Duan, W. Wang, J. Am. Chem. Soc. 2006, 128, 12652;
37. i) G. Bartoli, M. Bosco, A. Carlone, A. Cavalli, M. Locatelli, A. Mazzanti, P. Ricci, L. Sambria, P. Melchiorre, Angew. Chem. 2006, 118, 5088;
38. Angew. Chem. Int. Ed. 2006, 45, 4966;
39. for a review, see: j) M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550;
40. Angew. Chem. Int. Ed. 2006, 45, 1520.
41. A completed theoretical prediction of the hydride affinities of p-and o-quinones can be found in X.-Q. Zhu, C.-H. Wan, H. Lian, J.-P. Cheng, J. Org. Chem. 2007, 72, 945.
42. A DFT calculation (B3LYP) of the relative energies of the acetal compound 3g and its corresponding ketone reveals major stability of the acetal.
43. CCDC 643673 (ent-3g) and CCDC 643674 (rac-5) contain the supplementary crystallographic 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.
44. For a general review of spiro compounds and different synthesis approaches, see: a) L. F. Silva, Jr., Synthesis 2001, 671;
45. b) R. Pradhan, M. Patra, A. K. Behera, B. K. Mishra, R. H. Behera, Tetrahedron 2006, 62, 779.