Intramolecular bromo-amination of 1,4-cyclohexadiene aminal: One-pot discrimination of two olefins and concise asymmetric synthesis of (-)-γ-lycorane

Chemical Communications

Volumn , Issue 8, 2006, Pages 832-834

  Fujioka, Hiromichi ^a   Murai, Kenichi ^a   Ohba, Yusuke ^a   Hirose, Hideki ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 CYCLOHEXADIENE; ALDEHYDE DERIVATIVE; ALKENE; AMINE; CARBON; CYCLOHEXA 2,5 DIENYL 1 METHYLALDEHYDE; CYCLOHEXANE; GAMMA LYCORANE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL REACTION; MOLECULAR DYNAMICS; MOLECULE; PURIFICATION; SYNTHESIS;

EID: 32844462569     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b512161b     Document Type: Article

References (19)

1. Recent reviews, see: (a) M. Antiss, J. M. Hollamd, A. Nelson and J. R. Titshmarsh, Synlett, 2003, 8, 1213;
2. (b) K. Mikami and A. Yoshida, J. Synth. Org. Chem., Jpn., 2002, 60, 732;
3. (c) N. A. Rahman and Y. Landais, Curr. Org. Chem., 2002, 6, 1369;
4. (d) A. C. Spivey and B. I. Andrews, Angew. Chem., Int. Ed., 2001, 40, 3131;
5. (e) M. C. Willis, J. Chem. Soc., Perkin Trans. 1, 1999, 1765.
6. (a) H. Fujioka, N. Kotoku, Y. Sawama, H. Kitagawa, Y. Ohba, T.-L. Wang, Y. Nagatomi and Y. Kita, Chem. Pharm. Bull., 2005, 53, 952;
7. (b) H. Fujioka, N. Kotoku, Y. Sawama, Y. Nagatomi and Y. Kita, Tetrahedron Lett., 2002, 43, 4825.
8. For another desymmetrization using intramolecular haloetherification by us, see: H. Fujioka, Y. Ohba, H. Hirose, K. Murai and Y. Kita, Angew. Chem., Int. Ed., 2005, 44, 734.
9. Oxidation of aminal to dihydroimidazole by NXS (X = Cl, Br, I) including this transformation was recently accepted; H. Fujioka, K. Murai, Y. Ohba, A. Hiramatsu and Y. Kita, Tetrahedron Lett., 2005, 46, 2197.
10. 3SnH, AIBN.
11. R. Roger and D. G. Neilson, Chem. Rev., 1961, 61, 179-211.
12. For recent racemic syntheses, see: (a) Z. Shao, J. Chen, R. Huang, C. Wang, L. Li and H. Zhang, Synlett, 2003, 2228;
13. (b) A. Padowa, M. A. Brodeney and S. M. Lynch, J. Org. Chem., 2001, 66, 1716;
14. (c) J. Cassayre and S. Z. Zard, Synlett, 1999, 501;
15. (d) X. Hoang-Chong, B. Quiclet-Sire and S. Z. Zard, Tetrahedron Lett., 1999, 40, 248;
16. (e) J. Cossey, L. Tresnard and D. G. Pardo, Eur. J. Org. Chem., 1999, 1925 and references therein.
17. For recent asymmetric syntheses, see: (a) M. G. Banwell, J. E. Harvey and D. C. R. Hockless, J. Org. Chem., 2000, 65, 4241;
18. (b) M. Ikeda, S. Ohtani, T. Sato and H. Ishibashi, Synthesis, 1998, 1803;
19. (c) H. Yamazaki, H. Satoh, Y. Sato, S. Nukui, M. Shibasaki and M. Mori, J. Org. Chem., 1995, 60, 2016.