Catalytic asymmetric nitroso-Diels-Alder reaction with acyclic dienes

Angewandte Chemie - International Edition

Volumn 44, Issue 43, 2005, Pages 7082-7085

  Yamamoto, Yuhei ^a   Yamamoto, Hisashi ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

Amino alcohols; Asymmetric catalysis; Cycloaddition; Dienes; Nitroso compounds

Indexed keywords

ALCOHOLS; CATALYSIS; REACTION KINETICS;

ACYCLIC DIENES; AMINO ALCOHOLS; CYCLOADDITION;

AROMATIC COMPOUNDS;

EID: 27744475777     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501345     Document Type: Article

References (39)

1. a) G. Kresze, J. Firl, Tetrahedron 1968, 24, 1043-1050;
2. b) H. Nitsch, G. Kresze, Angew. Chem. 1976, 88, 801;
3. Angew. Chem. Int. Ed. Engl. 1976, 15, 760.
4. For reviews, see: a) J. Streith, A. Defoin, Synthesis 1994, 1107-1117;
5. b) P. F. Vogt, M. J. Miller, Tetrahedron 1998, 54, 1317-1348;
6. for recent reports, see: c) A. A. P. Meekel, M. Resmini, U. K. Pandit, Bioorg. Med. Chem. 1996, 4, 1051-1057;
7. d) D. Zhang, C. Süling, M. J. Miller, J. Org. Chem. 1998, 63, 885-888;
8. e) S. Aoyagi, R. Tanaka, M. Naruse, C. Kibayashi, J. Org. Chem. 1998, 63, 8397-8406;
9. f) S. J. Gouverneur, J. McCarthy, C. Mineur, D. Belloti, G. Dive, L. Ghosez, Tetrahedron 1998, 54, 10537-10554;
10. g) C. Arribas, M. C. Carreno, J. L. García-Ruano, J. F. Rodríguez, M. Santos, M. A. Sanz-Tejedor, Org. Lett. 2000, 2, 3165-3168;
11. h) Y.-C. Wang, T.-M. Lu, S. Elango, C.-K. Lin, C.-T. Tsai, Y.-H. Yan, Tetrahedron: Asymmetry 2002, 13, 691-695;
12. i) A. P. Lightfoot, R. G. Pritchard, H. Wan, J. E. Warren, A. Whiting, Chem. Commun. 2002, 2072-2073;
13. j) K. R. Flower, A. P. Lightfoot, H. Wan, A. Whiting, J. Chem. Soc. Perkin Trans. 1 2002, 2058-2064;
14. k) X. Ding, Y. Ukaji, S. Fujinami, K. Inomata, Chem. Lett. 2003, 32, 582-583;
15. l) C. Miller, R. A. Batey, Org. Lett. 2003, 5, 699-702;
16. m) Y. Yamamoto, N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 5962-5963;
17. n) C. Geraldine, D. Marion, B. Nicolas, K. Cyrille, Org. Lett. 2004, 6, 2449-2451;
18. o) C. P. Chow, K. J. Shea, J. Am. Chem. Soc. 2005, 127, 3678-3679.
19. Y. Yamamoto, H. Yamamoto, J. Am. Chem. Soc. 2004, 126, 4128-4129.
20. A. G. Dossetter, T. F. Jamison, E. N. Jacobsen, Angew. Chem. 1999, 111, 2549-2552;
21. Angew. Chem. Int. Ed. 1999, 38, 2398-2400.
22. a) D. L. Boger, M. Patel, F. Takusagawa, J. Org. Chem. 1985, 50, 1911-1916;
23. b) K. F. McClure, S. J. Danishefsky, J. Org. Chem. 1991, 56, 850-853;
24. c) V. Gouverneur, L. Ghosez, Tetrahedron: Asymmetry 1991, 2, 1173-1176;
25. d) I. Cabanal-Duvillard, J.-F. Berrien, L. Ghosez, H.-P. Husson, J. Royer, Tetrahedron 2000, 56, 3763-3769;
26. e) A. G. Leach, K. N. Houk, J. Org. Chem. 2001, 66, 5192-5200.
27. T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264-267.
28. a) S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Gênet, N. Champion, P. Dellis, Angew. Chem. 2004, 116, 324-329;
29. Angew. Chem. Int. Ed. 2004, 43, 320-325;
30. b) F. Leroux, J. Gorecka, M. Schlosser, Synthesis 2004, 326-328;
31. c) S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Gênet, N. Champion, N. P. Dellis, Proc. Natl. Acad. Sci. 2004, 101, 5799-5804.
32. CCDC-271386 (3g), -271387 (6), and -271388 (9) 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.
33. 2: a) Y. S. Lee, L. F. Peng, Y. Kishi, J. Org. Chem. 1997, 62, 5666-5667, and references therein;
34. galantin I: b) N. Sakai, Y. Ohfune, J. Am. Chem. Soc. 1992, 114, 998-1010, and references therein.
35. For a review on use of the TIPS group in organic chemistry, see: C. Rücker, Chem. Rev. 1995, 95, 1009., and references therein.
36. For a review on π nucleophilicity, see: H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77.
37. A similar observation of the relationship between the enantioselectivity and size of the silicon group was observed: a) E. J. Corey, A. Guzman-Perez, T.-P. Loh, J. Am. Chem. Soc. 1994, 116, 3611-3612;
38. a diene that bears the OTBS group and reacts through a more pericyclic pathway than the OTMS group has been reported: b) S. Danishefsky, K.-U. Chao, G. Schulte, J. Org. Chem. 1985, 50, 4650-4652.
39. The NOESY experiment was conducted with both dienes (see Supporting Information).