Abstract
The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2-dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2-diols was proposed.
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M. Tokunaga, J. F. Larrow, F. Kakiuchi, and E. N. Jacobsen, Science, 1997, 277, 936; (b) E. N. Jacobsen, Acc. Chem. Res., 2000, 33, 421; (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.
Pharmaceutical Manufacturing Encyclopedia, Ed. M. Sitting, Noyes Publications, Park Ridge, 1988, 1, 2.
The Merck Index, 12th ed., Ed. S. Budavari, Merck and Co., Inc., Whitehouse Station, 1996, 5895; 4582; 2230.
A. A. Bredikhin, Z. A. Bredikhina, S. N. Lazarev, and D. V. Savel'ev, Mendeleev Commun., 2003, 104.
J. Jaques, A. Collet, and S. H. Wilen, Enantiomers, Racemates, and Resolutions, Krieger Publishing Co., Malabar (FL), 1994, 447.
L. Perez-Garcia and D. B. Amabilino, Chem. Soc. Rev., 2002, 31, 342.
W. L. Nelson, J. E. Wennerstrom, and S. R. Sankar, J. Org. Chem., 1977, 42, 1006.
F. Theil, J. Weidner, S. Ballschuh, A. Kunath, and H. Schick, J. Org. Chem., 1994, 59, 388; (b) L. Salazar, J. L. Bermudes, C. Ramirez, E. F. Llama, and J. V. Sinisterra, Tetrahedron Asymmetry, 1999, 10, 3507.
G. Egri, A. Kolbert, J. Balint, E. Fogassy, L. Novak, and L. Poppe, Tetrahedron Asymmetry, 1998, 9, 271.
J. M. Klunder, S. Y. Ko, and K. B. Sharpless, J. Org. Chem., 1986, 51, 3710; (b) J. Chen and W. Shum, Tetrahedron Lett., 1995, 36, 2379; (c) K. Kitaori, Y. Furukawa, H. Yoshimoto, and J. Otera, Tetrahedron, 1999, 55, 14381.
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.)].
C. C. Price and L. R. Becker, J. Polym. Sci., Part A-1, 1969, 7, 575.
Y.-J. Hu, X.-D. Huang, Z.-J. Yao, and Y.-L. Wu, J. Org. Chem., 1998, 63, 2456.
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.
Beilst., V,17(3), 15.
L. He, H.-S. Byun, and R. Bittman, J. Org. Chem., 1998, 63, 5696.
Z.-M. Wong, X.-L. Zhang, and K. B. Sharpless, Tetrahedron Lett., 1993, 34, 2267.
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.)].
J.-M. Brunel, O. Pardigon, M. Maffei, and G. Buono, Tetrahedron Asymmetry, 1992, 3, 1243.
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.)].
P. H. J. Carlsen and K. Aase, Acta Chem. Scand., 1993, 47, 737.
The Merck Index, 12th ed., Ed. S. Budavari, Merck and Co., Inc., Whitehouse Station, 1996, (a) 9653; (b) 6345.
R. Howe and B. S. Rao, J. Med. Chem., 1968, 11, 1118.
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Bredikhin, A.A., Strunskaya, E.I., Novikova, V.G. et al. Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes. Russian Chemical Bulletin 53, 213–218 (2004). https://doi.org/10.1023/B:RUCB.0000024851.29744.21
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DOI: https://doi.org/10.1023/B:RUCB.0000024851.29744.21