Lewis acid catalyzed asymmetric cycloadditions of nitrones: α′-hydroxy enones as efficient reaction partners

Angewandte Chemie - International Edition

Volumn 44, Issue 38, 2005, Pages 6187-6190

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   Arceo, Elena ^b   García, Jesús M ^b   López, Rosa ^a   González, Alberto ^b   Linden, Anthony ^c  

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

^b PUBLIC UNIVERSITY OF NAVARRE   (Spain)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Asymmetric catalysis; Cycloaddition; Hydroxy enones; Lewis acids; Synthetic methods

Indexed keywords

ASYMMETRIC CATALYSIS; HYDROXY ENONES; LEWIS ACIDS; NITRONES; SYNTHETIC METHODS;

ADDITION REACTIONS; ALDEHYDES; CARBOXYLIC ACIDS; CATALYSIS; KETONES;

NITROGEN COMPOUNDS;

ACID; NITROGEN OXIDE; NITRONES;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ACIDS; CATALYSIS; MOLECULAR STRUCTURE; NITROGEN OXIDES; STEREOISOMERISM;

EID: 25844444557     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502308     Document Type: Article

References (41)

1. For reviews, see: a) K. V. Gothelf, K. A. Jørgensen, Chem. Rev. 1998, 98, 863-909;
2. b) K. V. Gothelf, K. A. Jørgensen, Chem. Commun. 2000, 1449-1458;
3. c) S. Kanemasa, Synlett 2002, 1371-1387;
4. d) K. V. Gothelf in Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi, K. A. Jørgensen), Wiley-VCH, Weinheim, 2002, pp. 211-247;
5. e) K. V. Gothelf, K. A. Jørgensen in Synthetic Applications of 1,3-Dipolar Cycloaddition, Chemistry toward Heterocycles and Natural Products, (Eds.: A. Padwa, W. H. Pearson), Wiley, Hoboken, NJ, 2003, pp. 817-900.
6. a) J. N. Martin, R. C. F. Jones in Synthetic Applications of 1,3-Dipolar Cycloaddition, Chemistry toward Heterocycles and Natural Products, (Eds.: A. Padwa, W. H. Pearson), Wiley, Hoboken, NJ, 2003, pp. 1-82;
7. b) S. Karlsson, H.-E. Högberg, Org. Prep. Proc. Int. 2001, 33, 103-172.
8. For illustrative examples using stoichiometric chiral auxiliaries, see: a) T. Gefflaut, U. Bauer, K. Airola, A. M. P. Koskinen, Tetrahedron: Asymmetry 1996, 7, 3099-3102;
9. b) A. Carriere, A. Virgili, M. Figueredo, Tetrahedron: Asymmetry 1996, 7, 2793-2796;
10. c) T. Tejero, A. Dondoni, I. Rojo, F. L. Merchán, P. Merino, Tetrahedron 1997, 53, 3301-3318;
11. d) P. Merino, S. Anoro, S. Franco, F. L. Merchán, T. Tejero, V. Tuñón, J. Org. Chem. 2000, 65, 1590-1596;
12. e) O. Tamura, A. Kanoh, M. Yamashita, H. Ishibashi, Tetrahedron 2004, 60, 9997-10 003.
13. For illustrative examples using chiral catalysts, see: a) K. V. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 1998, 63, 5483-5488, and references therein;
14. b) T. Saito, T. Yamada, S. Miyazaki, T. Otani, Tetrahedron Lett. 2004, 45, 9585-9587;
15. c) G. Desimoni, G. Faita, M. Mella, M. Boiocchi, Eur. J. Org. Chem. 2005, 1020-1027;
16. d) F. Viton, G. Bernardinelli, E. P. Kündig, J. Am. Chem. Soc. 2002, 124, 4968-4969;
17. e) M. Shirahase, S. Kanemasa, Y. Oderaotoshi, Org. Lett. 2004, 6, 675-678;
18. f) D. Carmona, M. P. Lamata, F. Viguri, R. Rodríguez, L. A. Oro, A. I. Balana, F. J. Lahoz, T. Tejero, P. Merino, S. Franco, I. Montesa, J. Am. Chem. Soc. 2004, 126, 2716-2717.
19. a) W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875;
20. b) S. Karlsson, H.-E. Högberg, Eur. J. Org. Chem. 2003, 2782-2791.
21. II: a) H. Suga, T. Nakajima, K. Itoh, A. Kakehi, Org. Lett. 2005, 7, 1431-1434;
22. b) S. Iwasa, H. Maeda, K. Nishiyama, S. Tsushima, Y. Tsukamoto, H. Nishiyama, Tetrahedron 2002, 58, 8281-8287;
23. c) S. Kanemasa, Y. Oderaotoshi, J. Tanaka, E. Wada, J. Am. Chem. Soc. 1998, 120, 12 355-12 356;
24. II: d) K. Hori, H. Kodama, T. Ohta, I. Furukawa, J. Org. Chem. 1999, 64, 5017-5023;
25. II: e) S. Iwasa, Y. Ishima, H. S. Widagdo, K. Aoki, H. Nishiyama, Tetrahedron Lett. 2004, 45, 2121-2124;
26. for complexes of lanthanides: f) H. Kodama, J. Ito, K. Hori, T. Ohta, I. Furukawa, J. Organomet. Chem. 2000, 603, 6-12;
27. g) S. Kobayashi, M. Kawamura, J. Am. Chem. Soc. 1998, 120, 5840-5841;
28. II: h) M. P. Sibi, Z. Ma, C. P. Jasperse, J. Am. Chem. Soc. 2004, 126, 718-719;
29. II: i) Z.-Z. Huang, Y.-B. Kang, J. Zhou, M.-C Ye, Y. Tang, Org. Lett. 2004, 6, 1677-1679.
30. Nitrones are basic in nature and may show competitive coordination to the metal, thus provoking inactivation of the Lewis acid; for more information on this subject, see: S. Kanemasa, T. Uemura, E. Wada, Tetrahedron Lett. 1992, 33, 7889-7892.
31. For Diels-Alder reactions, see: a) C. Palomo, M. Oiarbide, J. M. García, A. González, E. Arceo, J. Am. Chem. Soc. 2003, 125, 13 942-13 943;
32. for conjugate additions of carbamates, see: b) C. Palomo, M. Oiarbide, R. Halder, M. Kelso, E. Gómez-Bengoa, J. M. García, J. Am. Chem. Soc. 2004, 126, 9188-9189;
33. for Friedel-Crafts reactions, see: c) C. Palomo, M. Oiarbide, B. G. Kardak, J. M. García, A. Linden, J. Am. Chem. Soc. 2005, 127, 4154-4155.
34. Compound 1 is readily prepared in two steps (75 %) from (1R)-(+)-camphor and methoxyallene, two commodity chemicals that are available in bulk; see: C. Palomo, M. Oiarbide, J. M. García, A. González, A. Lecumberri, A. Linden, J. Am. Chem. Soc. 2002, 124, 10 288-10 289.
35. To avoid decomposition of the nitrone and ensure good yields and high selectivities, the presence of 4-Å molecular sieves was required in these instances; for the first observation and discussion of the effect of molecular sieves in Lewis acid catalyzed nitrone cycloadditions, see: a) K. V. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 1996, 61, 346-355;
36. b) See Ref. [6g].
37. For the concept of privileged chiral catalysts, see: T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691-1693.
38. For other systems examined, see the Supporting Information.
39. II complexes, see Ref. [6b];
40. II-promoted reaction of diphenyl nitrone with N-acryloyl oxazolidinone leads to a regioselectivity of greater than 98:2, an endo/exo ratio of 97:3, and 86 % ee for the endo isomer.
41. CCDC-280037-280040 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.