Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes

Russian Chemical Bulletin

Volumn 53, Issue 1, 2004, Pages 213-218

  Bredikhin, A A ^a   Strunskaya, E I ^a   Novikova, V G ^a   Azancheev, N M ^a   Sharafutdinova, D R ^a   Bredikhina, Z A ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

3 aryloxypropane 1,2 diols; 31P NMR; Aryl glycidyl ethers; Chiral Co(salen) catalyst; Enantiomeric purity; Enantioselective hydrolysis; Moprolol; Toliprolol

Indexed keywords

ETHER DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; PHOSPHOLE DERIVATIVE;

ARTICLE; CATALYST; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 3543126100     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:RUCB.0000024851.29744.21     Document Type: Article

References (34)

1. (a) M. Tokunaga, J. F. Larrow, F. Kakiuchi, and E. N. Jacobsen, Science, 1997, 277, 936;
2. (b) E. N. Jacobsen, Acc. Chem. Res., 2000, 33, 421;
3. (c) S. E. Shaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, and E. N. Jacobsen, J. Am. Chem. Soc., 2002, 124, 1307.
4. Pharmaceutical Manufacturing Encyclopedia, Ed. M. Sitting, Noyes Publications, Park Ridge, 1988, 1, 2.
5. The Merck Index, 12th ed., Ed. S. Budavari, Merck and Co., Inc., Whitehouse Station, 1996, 5895; 4582; 2230.
6. A. A. Bredikhin, Z. A. Bredikhina, S. N. Lazarev, and D. V. Savel'ev, Mendeleev Commun., 2003, 104.
7. J. Jaques, A. Collet, and S. H. Wilen, Enantiomers, Racemates, and Resolutions, Krieger Publishing Co., Malabar (FL), 1994, 447.
8. L. Perez-Garcia and D. B. Amabilino, Chem. Soc. Rev., 2002, 31, 342.
9. W. L. Nelson, J. E. Wennerstrom, and S. R. Sankar, J. Org. Chem., 1977, 42, 1006.
10. (a) F. Theil, J. Weidner, S. Ballschuh, A. Kunath, and H. Schick, J. Org. Chem., 1994, 59, 388;
11. (b) L. Salazar, J. L. Bermudes, C. Ramirez, E. F. Llama, and J. V. Sinisterra, Tetrahedron Asymmetry, 1999, 10, 3507.
12. G. Egri, A. Kolbert, J. Balint, E. Fogassy, L. Novak, and L. Poppe, Tetrahedron Asymmetry, 1998, 9, 271.
13. (a) J. M. Klunder, S. Y. Ko, and K. B. Sharpless, J. Org. Chem., 1986, 51, 3710;
14. (b) J. Chen and W. Shum, Tetrahedron Lett., 1995, 36, 2379;
15. (c) K. Kitaori, Y. Furukawa, H. Yoshimoto, and J. Otera, Tetrahedron, 1999, 55, 14381.
16. Z. A. Bredikhina, D. V. Savel'ev, and A. A. Bredikhin, Zh. Org. Khim., 2002, 38, 233 [Russ. J. Org. Chem., 2002, 38 (Engl. Transl.)].
17. Z. A. Bredikhina, D. V. Savel'ev, and A. A. Bredikhin, Zh. Org. Khim., 2002, 38, 233 [Russ. J. Org. Chem., 2002, 38 (Engl. Transl.)].
18. C. C. Price and L. R. Becker, J. Polym. Sci., Part A-1, 1969, 7, 575.
19. Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 1998, 63, 2456.
20. E. Souri, M. Sharifzadeh, H. Farsam, and N. Gharavi, J. Pharm. Pharmacol., 1999, 51, 853; A. Barret and V. A. Cullum, Br. J. Pharmacol., 1968, 34, 43; J. Nakano, M. Mimura, M. Hayashida, M. Fujii, K. Kimura, and T. Naranishi, Chem. Pharm. Bull., 1988, 36, 1399.
21. E. Souri, M. Sharifzadeh, H. Farsam, and N. Gharavi, J. Pharm. Pharmacol., 1999, 51, 853; A. Barret and V. A. Cullum, Br. J. Pharmacol., 1968, 34, 43; J. Nakano, M. Mimura, M. Hayashida, M. Fujii, K. Kimura, and T. Naranishi, Chem. Pharm. Bull., 1988, 36, 1399.
22. E. Souri, M. Sharifzadeh, H. Farsam, and N. Gharavi, J. Pharm. Pharmacol., 1999, 51, 853; A. Barret and V. A. Cullum, Br. J. Pharmacol., 1968, 34, 43; J. Nakano, M. Mimura, M. Hayashida, M. Fujii, K. Kimura, and T. Naranishi, Chem. Pharm. Bull., 1988, 36, 1399.
23. Beilst., V, 17(3), 15.
24. L. He, H.-S. Byun, and R. Bittman, J. Org. Chem., 1998, 63, 5696.
25. Z.-M. Wong, X.-L. Zhang, and K. B. Sharpless, Tetrahedron Lett., 1993, 34, 2267.
26. Z. A. Bredikhina, V. G. Novikova, N. M. Azancheev, and A. A. Bredikhin, Zh. Obshch. Khim., 2002, 72, 1288 [Russ. J. Gen. Chem., 2002, 72 (Engl. Transl.)].
27. Z. A. Bredikhina, V. G. Novikova, N. M. Azancheev, and A. A. Bredikhin, Zh. Obshch. Khim., 2002, 72, 1288 [Russ. J. Gen. Chem., 2002, 72 (Engl. Transl.)].
28. J.-M. Brunel, O. Pardigon, M. Maffei, and G. Buono, Tetrahedron Asymmetry, 1992, 3, 1243.
29. A. A. Bredikhin, E. I. Strunskaya, N. M. Azancheev, and Z. A. Bredikhina, Izv. Akad. Nauk, Ser. Khim., 1998, 172 [Russ. Chem. Bull., 1998, 47, 174 (Engl. Transl.)].
30. A. A. Bredikhin, E. I. Strunskaya, N. M. Azancheev, and Z. A. Bredikhina, Izv. Akad. Nauk, Ser. Khim., 1998, 172 [Russ. Chem. Bull., 1998, 47, 174 (Engl. Transl.)].
31. P. H. J. Carlsen and K. Aase, Acta Chem. Scand., 1993, 47, 737.
32. The Merck Index, 12th ed., Ed. S. Budavari, Merck and Co., Inc., Whitehouse Station, 1996, (a) 9653; (b) 6345.
33. The Merck Index, 12th ed., Ed. S. Budavari, Merck and Co., Inc., Whitehouse Station, 1996, (a) 9653; (b) 6345.
34. R. Howe and B. S. Rao, J. Med. Chem., 1968, 11, 1118.