Catalytic enantioselective three-component hetero-[4+2] cycloaddition/allylboration approach to α-hydroxyalkyl pyrans: Scope, limitations, and mechanistic proposal

Chemistry - A European Journal

Volumn 12, Issue 11, 2006, Pages 3132-3142

  Gao, Xuri ^a   Hall, Dennis G ^a   Deligny, Michael ^b   Favre, Annaick ^b   Carreaux, François ^b   Carboni, Bertrand ^b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UMR 6509 Organometalliques et Catalyse Chimie et Electrochimie Moleculaires   (France)

Author keywords

Asymmetric catalysis; Boron; Cycloaddition; Enol ethers; Pyrans

Indexed keywords

ALDEHYDES; BORON; ETHERS; ISOMERS; SUBSTRATES;

ASYMMETRIC CATALYSIS; CYCLOADDITION; ENOL ETHERS; TRANSITION STATE;

CATALYST ACTIVITY;

ALLYL COMPOUND; BORON; PYRAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALLYL COMPOUNDS; BORON; CATALYSIS; PYRANS; STEREOISOMERISM;

EID: 33645678207     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501197     Document Type: Article

References (46)

1. M. C. Elliott, J. Chem. Soc. Perkin Trans. 1 2002, 2301-2323.
2. For a review see: K.A. Jørgensen, Angew. Chem. 2000, 112, 3702-3733;
3. Angew. Chem. Int. Ed. 2000, 39, 3558-3588.
4. D. B. Stierle, A.A. Stierle, Experienlia 1992, 48, 1165-1169.
5. a) G. R. Pettit, J.-P. Xu, J.-C. Chapuis, R. K. Pettit, L. P. Tackelt, D. L. Doubek, J. N. A. Hooper, J. M. Schmidt, J. Med. Chem. 2004, 47, 1149-1152;
6. b) R. H. Cichewicz, F. A. Valeriote, P. Crews. Org. Lett 2004, 6, 1951-1954.
7. a) X. Gao, D. G. Hall, J. Am. Chem. Soc. 2003, 125, 9308-9309;
8. b) M. Deligny, F. Carreaux, L. Toupet, B. Carboni, Adv. Synth. Catal 2003, 345, 1215-1219.
9. a) B. B. Touré, H. R. Hoveyda, J. Tailor, A. Ulaczyk-Lesanko, D. G. Hall, Chem. Eur. J. 2003, 9, 466-474;
10. b) M. Gravel, B. B. Touré, D. G. Hall, Org. Prep. Proced. Int. 2004, 36, 573-579.
11. M. Deligny, F. Carreaux, B. Carboni, L. Toupet, G. Dujardin, Chem. Commun. 2003, 276-277.
12. a) M. Vaultier, F. Truchet, B. Carboni, R. W. Hoffmann, I. Denne, Tetrahedron Lett. 1987, 28, 4169-4172;
13. b) J.-Y. Lallemand, Y. Six, L. Ricard, Eur. J. Org. Chem. 2002. 503-513;
14. c) X. Gao, D. G. Hall, Tetrahedron Lett. 2003, 44, 2231-2235;
15. for reviews on boron functionalized 1,3-dienes in Diels-Alder reactions see: d) B. Carboni, F. Carreaux in Boronic Acids - Preparation and Applications in Organic Synthesis and Medicine (Ed.: D.G. Hall), Wiley-VCH. 2005. pp. 343-376;
16. e) G. Hilt, P. Bolze, Synthesis 2005, 2091-2115.
17. K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2002, 114, 3185-3187;
18. Angew. Chem. Int. Ed. 2002, 41, 3059-3061;.
19. R. W. Hoffmann, Pure Appl. Chem. 1988, 60, 123-130.
20. R. W. Hoffmann, J. J. Wolff. Chem. Ber. 1991, 124, 563-569.
21. For selected reviews on multicomponent reactions see: a) L. Weber, K. Illgen, M. Almstetter, Synlett 1999, 366-374;
22. b) H. Bienaymé. C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321-3329;
23. c) V. Nair, C. Rajesh, A. U. Vinod, S. Bindu, A. R. Sreekanth, J. S. Mathen, L. Balagopal, Acc. Chem. Res. 2003, 36, 899-907;
24. d) C. Hulme, V. Gore. Curr. Med. Chem. 2003, 10, 51-80;
25. e) J. P. Zhu, Eur. J. Org. Chem. 2003, 7, 1133-1144;
26. f) Multicomponent Reactions (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005.
27. M. Deligny, F. Carreaux, B. Carboni, Synlett 2005, 1462-1464.
28. X. Gao, D. G. Hall, J. Am. Chem. Soc. 2005, 127, 1628-1629.
29. P. B. Tripathy, D. S. Matteson, Synthesis 1990, 200-206.
30. This observation, however, is consistent with a limited study with allylhoronic acid 1,3-propanediol ester and benzaldehyde, which showed that polar weakly coordinating solvents gave the fastest reaction rate (THF < toluene < dichloromethane < ethyl ether): H. C. Brown, U. S. Racherla, P. J. Pellechia, J. Org. Chem. 1990, 55, 1868-1874.
31. a) J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 11586-11587;
32. b) T. Ishiyama. T.-a. Ahiko, N. Miyaura, J. Am. Chem. Soc. 2002, 124, 12414-12415.
33. CCDC 218262 contains the supplementary crystallographic data for this paper. These data can be found from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
34. For examples of catalytic enantioselective HDA reactions of cyclic enol ethers see: a) D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635-1649;
35. b) H. Audrain, J. Thorauge, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2000, 65, 4487-4497.
36. CCDC-284568 contains the supplementary crystallographic data for this paper. These data can be found from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
37. D. A. Evans, G. C. Andrew, B. Buckwalter. J. Am. Chem. Soc. 1974, 96, 5560-5561.
38. Isomeric 2-substituted acyclic enol ethers were found to be equally reactive with other substrates/catalysts: E. Wada, W. Pei, H. Yasuoka, U. Chin, S. Kanemasa, Tetrahedron 1996, 52, 1205-1220.
39. a) D. S. Matteson, J. O Wasserbillig, J. Org. Chem. 1963, 28, 366-369;
40. b)W. G. Woods, I. S. Bengelsdorf, J. Org. Chem. 1966, 31, 2769-2772;
41. c) D. S. Matteson, M. L. Talbot, J. Am. Chem. Soc. 1967, 89, 1123-1126.
42. D. S. Matteson, R. J. Moody, Organometallics 1982, 1, 20-28.
43. a) D. A. Singleton in Advances in Cycloaddition (Ed.: M. Lautens), Vol.4, JAI press, Greenwich, 1997, pp. 121-148;
44. b) M. A. Silva, S. C. Pellegrinet, J. M. Goodman, Arkivoc 2003, 556-565.
45. F. Carreaux, F. Possémé, B. Carboni, A. Arrieta, B. Lecea, F. Cossío, J. Org. Chem. 2002, 67, 9153-9161.
46. A. Rastelli, R. Gandolfi, M. Sarzi-Amade, B. Carboni, J. Org. Chem. 2001, 66, 2449-2458.