Synthesis of dendrimer-supported prolinols and their application in enantioselective reduction of ketones

Synlett

Volumn , Issue 8, 2006, Pages 1150-1154

  Wang, Guang Yin ^a   Liu, Xin Yuan ^a   Zhao, Gang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Amino alcohol; Asymmetric reduction; Dendrimer supported

Indexed keywords

AMINOALCOHOL; BORANE DERIVATIVE; DENDRIMER; KETONE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COLUMN CHROMATOGRAPHY; ENANTIOSELECTIVITY; REDUCTION; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 33744485822     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926253     Document Type: Article

References (47)

1. (a) Singh, V. K. Synthesis 1992, 605.
2. (b) Corey, E. J.; Helal, C. J. Angew. Chem. Int. Ed. 1998, 37, 1986.
3. (a) Trentmann, W.; Mehler, T.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2033.
4. (b) Mukund, P. S.; Gregory, R. C.; Pingrong, L. Tetrahedron Lett. 1999, 40, 2477.
5. Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217.
6. (a) Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1984, 2887.
7. (b) Itsuno, S.; Nakano, M.; Ito, K.; Hirao, A.; Owa, M.; Kanda, N.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1985, 2615.
8. (c) Itsuno, S.; Sakuri, Y.; Shimizu, K.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1990, 1859.
9. (d) Caze, C.; El Moualij, N.; Hodge, P.; Lock, C. J.; Ma, J. J. Chem. Soc., Perkin Trans. 1 1995, 345.
10. (e) Caze, C.; El Moualij, N.; Hodge, P.; Lock, C. J. Polymer 1995, 621.
11. (f) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
12. Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345.
13. (a) Chow, H.-F.; Mong, T. K.-K.; Nongrum, M. F.; Wan, C.-W. Tetrahedron 1998, 54, 8543.
14. (b) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendritic Molecules: Concepts, Syntheses, Perspectives; VCH: Weinheim, 1996.
15. (c) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A. III Angew. Chem., Int. Ed. Engl. 1990, 29, 138.
16. (d) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 993, 165, 193.
17. (e) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413.
18. (f) Balzani, V.; Denti, S. G.; Juris, A.; Serroni, S.; Venturi, M. Acc. Chem. Res. 1998, 31, 26.
19. (g) Ardoin, N.; Astruc, D. Bull. Soc. Chim. Fr. 1995, 132, 875.
20. (h) Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681.
21. (i) Schlüter, A.-D. Top. Curr. Chem. 1998, 197, 165.
22. (j) Fischer, M.; Vögtle, F. Angew. Chem. Int. Ed. 1999, 38, 884.
23. Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwen, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature (London) 1994, 372, 659.
24. (a) Peerlings, H. W. I.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1563.
25. (b) Brunner, H. J. Organomet. Chem. 1995, 500, 39.
26. (c) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285.
27. (d) Brunner, H.; Fürst, J. Tetrahedron 1994, 50, 4303.
28. (e) Brunner, H.; Net, G. Synthesis 1995, 423.
29. (f) Sanders-Hovens, M. S. T. H.; Jansen, J. F. G. A.; Vekemans, J. A. J. M.; Meijer, E. W. Polym. Mater. Sci. Eng. 1995, 73, 338.
30. (g) Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710.
31. (h) Rheiner, P. B.; Sellner, H.; Seebach, D. Helv. Chim. Acta 1997, 80, 2027.
32. (i) Rheiner, P. B.; Seebach, D. Polym. Mater. Sci. Eng. 1997, 77, 130.
33. (j) Suzuki, T.; Hirokawa, Y.; Ohtake, K.; Shibata, T.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 4033.
34. (k) Yamago, S.; Furukawa, M.; Azuma, A.; Yoshida, J.-I. Tetrahedron Lett. 1998, 39, 3783.
35. (l) Köllner, C.; Pugin, B.; Togni, A. J. Am. Chem. Soc. 1998, 120, 10274.
36. (m) Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387.
37. (n) Bolm, C.; Derrien, N.; Seger, A. Chem. Commun. 1999, 2087.
38. (o) Ji, B.-M.; Yuan, Y.; Ding, K.-L.; Meng, J.-B. Chem. Eur. J. 2003, 9, 5989.
39. (p) Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789.
40. (q) Deng, G.-J.; Fan, Q.-H.; Chen, X.-M.; Liu, D.-S.; Chan, A. S. C. Chem. Commun. 2002, 1570.
41. (r) Chen, Y.-C.; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Michael, C. K. C.; Chan, A. S. C. Chem. Commun. 2001, 1488.
42. (s) Chung, Y.-M.; Rhee, H.-K. Chem. Commun. 2002, 238.
43. Liu, X.-Y.; Chai, Z.; Zhao, G.; Zhu, S.-Z. J. Org. Chem. 2005, 70, 7432.
44. Wang, G.-Y.; Hu, J.-B.; Zhao, G. Tetrahedron: Asymmetry 2004, 15, 807.
45. (a) Hu, J.-B.; Zhao, G.; Yang, G.-S.; Ding, Z.-D. J. Org. Chem. 2001, 66, 303.
46. (b) Hu, J.-B.; Zhao, G.; Yang, G.-S.; Ding, Z.-D. Angew. Chem. Int. Ed. 2001, 40, 1109.
47. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.