Domino synthesis of bridged bicyclic tetrahydro-1,2-oxazines: Access to stereodefined 4-aminocyclohexanols

Organic Letters

Volumn 11, Issue 16, 2009, Pages 3694-3697

  Dias, Dwayne A ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOCYCLOHEXANOL; 4-AMINOCYCLOHEXANOL; CYCLOHEXANOL DERIVATIVE; CYCLOHEXYLAMINE DERIVATIVE; OXAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; CYCLOHEXANOLS; CYCLOHEXYLAMINES; MOLECULAR STRUCTURE; OXAZINES; STEREOISOMERISM;

EID: 68949128519     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901454y     Document Type: Article

References (41)

1. (a) Enders, D.; Grondal, C.; Huettl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
2. (b) Padwa, A.; Bur, S. K. Tetrahedron 2007, 63, 5341.
3. (c) de Meijere, A.; von Zezschwitz, P.; Braese, S. Acc. Chem. Res. 2005, 38, 413.
4. (d) Tietze, L. F.; Rackelmann, N. Pure Appl. Chem. 2004, 76, 1967.
5. (e) Tietze, L. F. Chem. Rev. 1996, 96, 115.
6. (a) Pohlhaus, P. D.; Johnson, J. S. J. Org. Chem. 2005, 70, 1057.
7. (b) Pohlhaus, P. D.; Sanders, S. D.; Parsons, A. T.; Li, W.; Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 8642, and references therein.
8. Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
9. (a) Carson, C. A.; Kerr, M. A. J. Org. Chem. 2005, 70, 8242.
10. (b) Kang, Y.-B.; Tang, Y.; Sun, X.-L. Org. Biomol. Chem. 2006, 4, 299, and references therein.
11. (a) Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122.
12. (b) Yu, M. B. L.; Pagenkopf, B. L. Org. Lett. 2003, 5, 5099.
13. Perreault, C.; Goudreau, S. R.; Zimmer, L. E.; Charette, A. B. Org. Lett. 2008, 10, 689.
14. Korotkov, V. S.; Larionov, O. V.; Hofmeister, A.; Magull, J.; de Meijere, A. J. Org. Chem. 2007, 72, 7504.
15. For reviews on the chemistry of donor-acceptor and electrophilic cyclopropanes, see: (a) Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321.
16. (b) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
17. (c) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
18. (d) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66.
19. With inversion of stereochemistry in the initial cyclopropane ring-opening event. See: Karadeolian, A.; Kerr, M. A. J. Org. Chem. 2007, 72, 10251.
20. (a) Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023.
21. (b) Wanapun, D.; Van Gorp, K. A.; Mosey, N. J.; Kerr, M. A.; Woo, T. K. Can. J. Chem. 2005, 83, 1752.
22. Young, I. S.; Kerr, M. A. Org. Lett. 2004, 6, 139.
23. Carson, C. A.; Kerr, M. A. Angew. Chem., Int. Ed. 2006, 45, 6560.
24. Young, I. S.; Williams, J. L.; Kerr, M. A. Org. Lett. 2005, 7, 953.
25. Young, I. S.; Kerr, M. A. J. Am. Chem. Soc. 2007, 129, 1465.
26. This mode of reactivity is currently under investigation. However, all attempts thus far have been unsuccessful.
27. For previous examples of carbocycle construction by intramolecular Mannich reaction, see: (a) Uchida, K.; Yokoshima, S.; Kan, T.; Fukuyama, T. Org. Lett. 2006, 8, 5311.
28. (b) Shibuguchi, T.; Mihara, H.; Kuramochi, A.; Sakuraba, S.; Ohshima, T.; Shibasaki, M. Angew. Chem., Int. Ed. 2006, 45, 4635.
29. (c) Taber, D. F.; Liang, J.-L.; Chen, B.; Cai, L. J. Org. Chem. 2005, 70, 8739.
30. (d) Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403.
31. (e) Winkler, J. D.; Axten, J. M. J. Am. Chem. Soc. 1998, 120, 6425.
32. (f) Winkler, J. D.; Haddad, N.; Ogilvie, R. J. Tetrahedron Lett. 1989, 30, 5703.
33. (a) Danishefsky, S. J.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829.
34. (b) Tian, X.; Hudlicky, T.; Koenigsberger, K. J. Am. Chem. Soc. 1995, 117, 3643, and references therein.
35. (a) Woodward, R. B.; Gougoutas, J. Z. J. Am. Chem. Soc. 1964, 86, 5030.
36. (b) Kishi, Y.; Fukutama, T.; Aratani, M.; Nakatsubo, F.; Goto, T.; Inoue, S.; Tanino, H.; Sugiura, S.; Kakoi, H. J. Am. Chem. Soc. 1972, 94, 9219.
37. (a) Tsuda, Y.; Nakai, A.; Ito, K.; Suzuki, F.; Haruna, M. Heterocycles 1984, 22, 1817.
38. (b) Hosoi, S.; Ishida, K.; Tsuda, Y. Chem. Pharm. Bull. 1992, 40, 3115.
39. It is worth noting that geminal disubstitution a to the aldehyde in 18 would eliminate the α-elimination pathway and allow the desired reaction to proceed. However, this was not investigated.
40. The use of three-carbon and five-carbon tethers were also investigated but were unsuccessful.
41. Wuts, P. G. M.; Jung, Y.-W. J. Org. Chem. 1988, 53, 1957.