Asymmetric synthesis of chromanones via N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reactions

Synlett

Volumn , Issue 15, 2006, Pages 2431-2434

  Enders, Dieter ^a   Niemeier, Oliver ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric synthesis; Benzoin reaction; Chromanones; N heterocyclic carbenes; Organocatalysis

Indexed keywords

3 HYDROXY 4 CHROMANONE DERIVATIVE; 4 CHROMANONE DERIVATIVE; BENZOIN; CARBENE; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 33749363854     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950403     Document Type: Article

References (49)

1. (a) Arduengo, A. J. III; Herlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 117, 361.
2. (b) Review: Arduengo, A. J. III; Krafczyk, R. Chem. Unserer Zeit 1998, 32, 6.
3. (c) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. Int. Ed. 1995, 34, 2021.
4. (d) Review: Canac, Y.; Soleilhavoup, M.; Conejero, S.; Bertrand, G. J. Organomet. Chem. 2004, 689, 3857.
5. Reviews: (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
6. (b) Zeitler, K. Angew. Chem. Int. Ed. 2005, 44, 7506.
7. (c) Enders, D.; Balensiefer, T.; Niemeier, O.; Christmann, M. Nucleophilic N-Heterocyclic Carbenes in Asymmetric Synthesis In Enantioselective Organocatalysis-Reactions and Experimental Procedures; Dalko, P., Ed.; Wiley-VCH: Weinheim, 2006, in press.
8. (a) Burstein, C.; Glorius, F. Angew. Chem. Int. Ed. 2004, 43, 6205.
9. (b) Sohn, S.S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
10. (c) He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131.
11. (d) Mattson, A. E.; Zuhl, A. M.; Reynolds, T. E.; Scheldt, K. A. J. Am. Chem. Soc. 2006, 128, 4932.
12. Singh, R.; Kissling, R. M.; Letellier, M.-A.; Nolan, S. P. J. Org. Chem. 2004, 69, 209.
13. Coulembier, O.; Dove, A. P.; Pratt, R. C.; Sentman, A. C.; Culkin, D. A.; Mespouille, L.; Dubois, P.; Waymouth, R. M.; Hedrick, J. L. Angew. Chem. Int. Ed. 2005, 44, 4964.
14. Fischer, C.; Smith, S. W.; Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 1472.
15. Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4558.
16. Song, J. J.; Tan, Z.; Reeves, J. T.; Gallou, F.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2005, 7, 2193.
17. (a) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314.
18. (b) Bharadwaj, A. R.; Scheidt, K. A. Org. Lett. 2004, 6, 2465.
19. Mattson, A. E.; Scheidt, K. A. Org. Lett. 2004, 6, 4363.
20. Enders, D.; Kallfass, U. Angew. Chem. Int. Ed. 2002, 41, 1743.
21. (a) Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899.
22. (b) Kerr, M. S.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2002, 35, 10298.
23. (c) Kerr, M. S.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 8876.
24. (d) de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 6284.
25. (e) Liu, Q.; Rovis, T. J. Am. Chem. Soc. 2006, 128, 2552.
26. (f) Short review: Christmann, M. Angew. Chem. Int. Ed. 2005, 44, 2632.
27. (a) Mennen, S. M.; Gipson, J. D.; Kim, Y. R.; Miller, S. J. J. Am. Chem. Soc. 2005, 127, 1654.
28. (b) Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696.
29. (a) Linghu, X.; Johnson, J. S. Angew. Chem. Int. Ed. 2003, 42, 2534.
30. (b) Linghu, X.; Potnick, J. R.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 3070.
31. (c) Linghu, X.; Bausch, C. C.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 1833.
32. Enzymatic cross-coupling: (a) Iding, H.; Dünnwald, T.; Greiner, L.; Liese, A.; Müller, M.; Siegert, P.; Grötzinger, J.; Demir, A. S.; Pohl, M. Chem. Eur. J. 2000, 6, 1483.
33. (b) Dünkelmann, P.; Kolter-Jung, D.; Nitsche, A.; Demir, A. S.; Siegert, P.; Lingen, B.; Baumann, M.; Pohl, M.; Müller, M. J. Am. Chem. Soc. 2002, 124, 12084.
34. (c) Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5289.
35. (a) Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432.
36. (b) Enders, D.; Niemeier, O. Synlett 2004, 2111.
37. (c) Hachisu, Y.; Bode, J. W.; Suzuki, K. Adv. Synth. Catal. 2004, 346, 1097.
38. (a) Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem. Int. Ed. 2006, 45, 1463.
39. (b) For a related study, see: Takikawa, H.; Hachisu, Y.; Bode, J. W.; Suzuki, K. Angew. Chem. Int. Ed. 2006, 45, 3492.
40. Reviews: (a) Fuji, K. Chem. Rev. 1993, 93, 2037.
41. (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem. Int. Ed. 1998, 37, 388.
42. (c) Christoffers, J.; Mann, A. Angew. Chem. Int. Ed. 2001, 40, 4591.
43. (d) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105.
44. (a) Heller, W.; Tamm, C. Fortschr. Chem. Org. Naturst. 1981, 40, 105.
45. (b) Davies, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55, 3715.
46. (a) Böhler, P.; Tamm, C. Tetrahedron Lett. 1967, 36, 3479.
47. (b) Crouch, N. R.; Bangnai, V.; Mulholland, D. A. Phytochemistry 1999, 51, 943.
48. 3 and α-bromo ketones in DMF at r.t.
49. CCDC 607797 (6a) and CCDC 607796 (6f) 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.