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Volumn 69, Issue 23, 2004, Pages 8165-8167

Organocatalytic asymmetric hydroxylation of β-keto esters: Metal-free synthesis of optically active anti-diols

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; DERIVATIVES; HYDROXYLATION; PEROXIDES; SYNTHESIS (CHEMICAL);

EID: 8644269567     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048655w     Document Type: Article
Times cited : (113)

References (35)
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    • See, e.g.: (a) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247. (b) Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808. (c) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8293. (d) Bøgevig, A.; Sundéen, H.; Córdova, A. Angew. Chem., Int. Ed. 2004, 43, 1109. (e) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112. (f) Cordova, A.; Sunden, H.; Engquist, M.; Ibrahem, I.; Casas, J. J. Am. Chem. Soc. 2004, 126, 8914.
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    • See, e.g.: (a) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247. (b) Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808. (c) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8293. (d) Bøgevig, A.; Sundéen, H.; Córdova, A. Angew. Chem., Int. Ed. 2004, 43, 1109. (e) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112. (f) Cordova, A.; Sunden, H.; Engquist, M.; Ibrahem, I.; Casas, J. J. Am. Chem. Soc. 2004, 126, 8914.
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    • see also: (b) Shapiro, R.; Annis, G. D.; Blaisdell, C. T.; Dumas, D. J.; Fuchs, J.; Grisweld, S. M.; Highly, G. W.; Hollinsed, W. C.; Mrowca, J. J.; Sternberg, J. A.; Woltkowski, P. ACS Symp. Ser. 2000, 800 (Synthesis and Chemistry of Agrochemicals VI), 178. (c) Taylor, E. G.; Birch, L. US Patent WO 03/040083, PTC/US02/35615, 2003.
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    • see also: (b) Shapiro, R.; Annis, G. D.; Blaisdell, C. T.; Dumas, D. J.; Fuchs, J.; Grisweld, S. M.; Highly, G. W.; Hollinsed, W. C.; Mrowca, J. J.; Sternberg, J. A.; Woltkowski, P. ACS Symp. Ser. 2000, 800 (Synthesis and Chemistry of Agrochemicals VI), 178. (c) Taylor, E. G.; Birch, L. US Patent WO 03/040083, PTC/US02/35615, 2003.
    • Taylor, E.G.1    Birch, L.2
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    • For use of chiral phase-transfer catalysis and molecular oxygen under basic conditions for hydroxylation of aromatic cyclic ketones, see: (a) Masui, M.; Ando, A.; Shioiri, T. Tetrahedron Lett. 1988, 29, 2835. (b) Christoffers, J.; Werner, T.; Unger, S.; Frey, W. Eur. J. Org. Chem. 2003, 424.
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    • For use of chiral phase-transfer catalysis and molecular oxygen under basic conditions for hydroxylation of aromatic cyclic ketones, see: (a) Masui, M.; Ando, A.; Shioiri, T. Tetrahedron Lett. 1988, 29, 2835. (b) Christoffers, J.; Werner, T.; Unger, S.; Frey, W. Eur. J. Org. Chem. 2003, 424.
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    • For the use of this approach for catalytic enantioselective addition of β-dicarbonyl compounds to alkynones, see: (a) Bella, M.; Jørgensen K. A. J. Am. Chem. Soc. 2004, 126, 5672.
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