Conformational toolbox of oxazaborolidine catalysts in the enantioselective reduction of α-bromo-ketone for the synthesis of (R,R)- formoterol

Tetrahedron Letters

Volumn 39, Issue 13, 1998, Pages 1705-1708

  Hett, Robert ^a   Senanayake, Chris H ^a   Wald, Stephen A ^a  

^a SUNOVION PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FORMOTEROL;

ARTICLE; CATALYSIS; CATALYST; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; STRUCTURE ANALYSIS;

EID: 0032568230     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00137-3     Document Type: Article

References (30)

1. (1) Nelson, H. S. N. Engl. J. Med. 1995, 333, 499.
2. (2) Trofast, J.; Österberg, K.; Källström, B.-L.; Waldeck, B. Chirality 1991, 3, 443.
3. (3) (a) Hirao, A; Itsuno, S; Nakahama, S.; Yamazaki, N. J. Chem. Soc. Chem. Comm. 1981, 315;
4. (b) Itsuno, S.; Sakurai, Y.; Ito, A.; Hirao, A; Nakahama, S. Bull. Chem. Soc. Jpn. 1987, 60, 395.
5. (4) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1988, 110, 1968.
6. (5) (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475;
7. (b) Deloux, L.; Srebnlk, M. Chem. Rev. 1993, 93, 763.
8. (C) Jones, T. K.; Mohan, J.J.; Xavier, L.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Tunner Jones, E.T.; Reamer, R. A.; Grabowski, E. J. J. Org. Chem. 1991, 56, 763;
9. (d) Salunkhe, A. M.; Burkhardt, E. R. Tetrahedron Lett. 1997, 38, 1523.
10. (6) (a) Sharpless, B. K.; King, S. B. Tetrahedron Lett. 1994, 35, 5611;
11. (b) Sharpless, B. K.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem. 1992, 57, 2768.
12. (7) Li, G.; Chang, H. T.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 451.
13. (8) (a) Jacobsen, E. N.; Larrow, F. J. J. Am. Chem. Soc. 1994, 116, 12129;
14. (b) Practical application of Jacobsen's epoxidation in the preparation of cis-1-amino-2-indanol see: Senanayake, C. H.; Smith, G. B.; Fredenburgh, L. E.; Liu, J.; Ryan, K. M.; Roberts, F. E.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 3271.
15. (9) Martinez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420.
16. (10) (a) Senanayake, C. H.; Roberts, F. E.; DiMichele, L. M.; Ryan, K. M.; Liu, J.; Fredenburgh, L. E.; Foster, B. S.; Douglas, A. W.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 3993;
17. (b) Senanayake, C. H.; DiMichele, L. M.; Liu, J.; Fredenburgh, L. E.; Ryan, K. M.; Roberts, F. E.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7615
18. (11) (a) Hong, Y.; Gao, Y.; Nie, X.; Zepp, C. M. Tetrahedron Lett. 1994, 35, 6631;
19. (b) Hong, Y.; Gao, Y.; Nie, X.; Zepp, C. M. Tetrahedron Lett. 1994, 35, 5551;
20. (c) Davis, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D. Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7619;
21. (d) Davis, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D. Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725;
22. (e) Davis, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D. Verhoeven, T. R.; Reider, P. J J. Chem. Comm. 1996, 1753.
23. (f) Ghosh, K. A.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1996, 37, 3815;
24. (g) Ghosh, K. A.; Chen, Y. Tetrahedron Lett. 1995, 36, 6811;
25. (h) Ghosh, K. A.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427 and references cited therein;
26. (I) McWilliams, J. C.; Armstrong, J. D.; Zheng, N.; Bhupathy, M.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 11970;
27. (J) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226
28. (12) Hett, R.; Fang, K. Q.; Gao, Y.; Hong, Y.; Butler, H. T.; Nie, X.; Wald, A. S Tetrahedron Lett. 1997, 38, 1125.
29. (13) Dongwei, C.; Tschaen, D.; Shi, Y.J.; Verhoeven, T.R.; Reamer, R. A.; Douglas. A. W. Tetrahedron Lett. 1993, 34, 3243.
30. 4 (2 × 20 mL) and with brine (20 mL). The organic layer was concentrated to a volume of 10 mL and cooled to 0 °C. Heptane (20 mL) was added at 0°C and the mixture aged for 2 h. The precipitate was filtered to give 3.1 g (90%) of crystalline (R)-2-Bromo(4-benzyloxy-3-formamidophenyl)ethanol. The ee increases by 2-3 % during the isolation process (ee before isolation are listed in Tables 1, 2 and 3). Enantiomeric excesses were determined by HPLC (Chiracel OJ column with 30 % EtOH in hexane at 1 ml/min, UV detection @ 230 nm, (R) = 21 min, (S) = 23 min).