Synthesis of enatiomerically enriched β-amino alcohol derivatives via chiral base mediated-asymmetric deprotonation of (benzyl methyl ether) tricarbonylchromium(0) complex and electrophilic trapping with imines

Journal of Chemical Research

Volumn , Issue 9, 2004, Pages 589-592

  Zhao, Cui Hua ^a   Liu, Li ^a   Chen, Yong Jun ^a   Wang, Dong ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

(benzyl methyl ether)tricarbonylchromium(0) complex; Chiral base; Imine; amino alcohol

Indexed keywords

(BENZYL METHYL ETHER)TRICARBONYLCHROMIUM COMPLEX; AMINOALCOHOL; CARBONYL DERIVATIVE; CHROMIUM DERIVATIVE; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHIRALITY; DEPROTONATION; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; X RAY DIFFRACTION;

EID: 9644310462     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/0308234042430485     Document Type: Article

References (33)

1. (a) J. Gante, Angew. Chem., Int. Ed., 1994, 33, 1669;
2. (b) T.D. Heightman and A.T. Vasella, Angew. Chem., Int. Ed., 1999, 38, 1750;
3. (c) T. Kolter and K. Sandhoff, Angew. Chem., Int. Ed., 1999, 38, 1532.
4. (a) M.T. Reez, Angew. Chem., Int. Ed., 1991, 30, 1531;
5. (b) D.J. Ager, I. Prakash and D.R. Schaad, Chem. Rev. 1996, 96, 835;
6. (c) S.C. Bergmeier, Tetrahedron 2000, 56, 2561;
7. (d) M.T. Reetz, Chem. Rev. 1999, 99, 1121;
8. (e) R. Bolch, Chem. Rev. 1998, 98, 1407.
9. For example, see: (a) T. Yoshie, T. Nobukazu and U. Motokazu, Org. Lett., 2002, 4, 835;
10. (b) A. Sonia, L. Esther and S. Nuria, Tetrahedron: Asymmetry, 2002, 13, 311;
11. (c) B. List, P. Pojarliev, W.T. Biller and H.J. Martin, J. Am. Chem. Soc., 2002, 124, 827;
12. (d) G.K. Friestad and S.E. Massari, Org. Lett., 2000, 2, 4237;
13. (e) B.M. Trost and C.B. Lee, J. Am. Chem. Soc., 1998, 120, 11798;
14. (f) S. Kobayashi, F. Furuta, T. Hayashi, M. Nishijima and K. Hanada, J. Am. Chem. Soc., 1998, 120, 908.
15. W. Chrisman, J.N. Camara, K. Marcellini, B. Singaram, C.T. Goralski, D.L. Hasha, P.R. Rudolf, L.W. Nicholson and K.K. Borodychuk, Tetrahedron Lett., 2001, 42, 5805.
16. Y. Tanaka, N. Taniguch, T. Kimura and M. Uemura, J. Org. Chem., 202, 67, 9227 and references cited there.
17. (a) S.E. Gibson and H. Ibrahim, Chem. Commun. 2002, 2465;
18. (b) K. Kamikawa and M. Uemura, Synlett 2000, 938;
19. (c) A.C. Comely and S.E. Gibson, J. Chem. Soc. Perkin Trans. 1, 1999, 223.
20. L.M. Cowton, S.E. Gibson, M.J. Schneider and M.H. Smith, Chem. Commun., 1996, 839.
21. (a) S.E. Gibson and M.H. Smitch, Org. Biomol. Chem., 2003, 1, 676;
22. (b) S.E. Gibson and E.G. Reddington, Chem. Commun., 2000, 989;
23. (c) A. Ariffin, A.J. Blake, R.A. Ewin, W.-S. Li and N.S. Simpkins, J. Chem. Soc., Perkin Trans. 1, 1999, 3177;
24. (d) S.E. Gibson, P. O'Brien, E. Rahimian and M.H. Smith, J. Chem. Soc., Perkin Trans. 1, 1999, 909;
25. (e) A. Ariffin, A.J. Blake, R.A. Ewin and N.S. Simpkins, Tetrahedron: Asymmetry 1998, 9, 2563.
26. (f) S.E. Gibson, P. Ham, G.R. Jefferson and M.H. Smith, J. Chem. Soc., Perkin Trans. 1, 1997, 2161;
27. (g) R.A. Ewqin, A.M. MacLeod, D.A. Price, N.S. Simpkins and A.P. Watt, J. Chem. Soc., Perkin Trans. 1, 1997, 401.
28. Y.-J. Chen, C.-H. Zhao, L. Liu and D. Wang, J. Chem. Res., 2003, 740.
29. J.B. Blagg, S.G. Davies, N.J. Holman, C.A. Laughton and B.E. Mobbs, J. Chem. Soc. Perkin Trans. 1, 1986, 1581.
30. (a) H. Dieck and J. Dierich, Chem. Ber., 1984, 117, 694;
31. (b) K. Bambridge, M.J. Begley and N.S. Simpkins, Tetrahedron, 1994, 35, 3391.
32. (a) S. Arrasate, E. Lete and N. Sotomayor, Tetrahedron: Asymmetry, 2002, 13, 311;
33. (b) R. Lou, A. Mi, Y. Jiang, Y. Qin, Z. Li, F. Fu and A.S.C. Chan, Tetrahedron, 2000, 56, 5857.