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Volumn 125, Issue 10, 2003, Pages 3090-3100

Palladium catalyzed kinetic and dynamic kinetic asymmetric transformations of γ-acyloxybutenolides. Enantioselective total synthesis of (+)-aflatoxin B1 and B2a

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL LIGANDS;

EID: 0037433509     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020988s     Document Type: Article
Times cited : (127)

References (54)
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  • 2
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    • For enzyme catalyzed KAT of butenolides, see: (a) Feringa, B. L.; de Lange, B.; de Jong, J. C. J. Org. Chem. 1989, 54, 2471. (b) Wijnand, S. F.; Kob, J.; de Lange, B.; Feringa, B. L. Tetrahedron 1994, 50, 4775. (c) van der Deen, H.; Hof, R. P.; van Oeveren, A.; Feringa, B. L.; Kellogg, R. M. Tetrahedron Lett. 1994, 35, 8441.
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    • Wijnand, S.F.1    Kob, J.2    De Lange, B.3    Feringa, B.L.4
  • 3
    • 0028075562 scopus 로고
    • For enzyme catalyzed KAT of butenolides, see: (a) Feringa, B. L.; de Lange, B.; de Jong, J. C. J. Org. Chem. 1989, 54, 2471. (b) Wijnand, S. F.; Kob, J.; de Lange, B.; Feringa, B. L. Tetrahedron 1994, 50, 4775. (c) van der Deen, H.; Hof, R. P.; van Oeveren, A.; Feringa, B. L.; Kellogg, R. M. Tetrahedron Lett. 1994, 35, 8441.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8441
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    • Searle, C., Ed.; American Chemical Society: Washington
    • (b) Busby, W. F.; Wogan, G. N. In Chemical Carcinogens, Searle, C., Ed.; American Chemical Society: Washington, 1984; Vol. 182, pp 945-1136.
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    • For enantioselective formal syntheses, see: (a) Marino, J. P. Pure Appl. Chem. 1993, 68, 667. (b) Civitello, E. R.; Rapoport, H. J. Org. Chem, 1994, 59, 3775. c. Bando, T.; Shishido, K. Synlett 1997, 665.
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  • 21
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    • For enantioselective formal syntheses, see: (a) Marino, J. P. Pure Appl. Chem. 1993, 68, 667. (b) Civitello, E. R.; Rapoport, H. J. Org. Chem, 1994, 59, 3775. c. Bando, T.; Shishido, K. Synlett 1997, 665.
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    • For enantioselective formal syntheses, see: (a) Marino, J. P. Pure Appl. Chem. 1993, 68, 667. (b) Civitello, E. R.; Rapoport, H. J. Org. Chem, 1994, 59, 3775. c. Bando, T.; Shishido, K. Synlett 1997, 665.
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  • 23
    • 0033605174 scopus 로고    scopus 로고
    • This transformation has been accomplished in two steps utilizing resolution and then palladium catalyzed reaction. (a) van der Deen, H.; van Oeveren, A.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 1755 (b) Cuiper, A. D.; Kellogg, R. M.; Feringa, B. L. Chem. Commun. 1998, 655.
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  • 24
    • 0001903683 scopus 로고    scopus 로고
    • This transformation has been accomplished in two steps utilizing resolution and then palladium catalyzed reaction. (a) van der Deen, H.; van Oeveren, A.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 1755 (b) Cuiper, A. D.; Kellogg, R. M.; Feringa, B. L. Chem. Commun. 1998, 655.
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  • 25
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    • For an example of coordination of enantiotopic olefin faces as the enantiodetermining step, see: Trost, B. M.; Asakawa, N. Synlett 1999, 1491.
    • (1999) Synlett , pp. 1491
    • Trost, B.M.1    Asakawa, N.2
  • 26
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    • and references therein
    • For examples of ionization of enantiotopic leaving groups as the enantio-determining step, see: (a) Trost, B. M.; Madsen, R.; Guile, S. D.; Brown, B. J. Am. Chem. Soc. 2000, 122, 5974, and references therein.
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    • For examples of palladium catalyzed DYKAT, see: (a) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10 834. (b) Trost, B. M.; Bunt, R. C.; Lemoine, R. C.; Calkins, T. L. J. Am. Chem. Soc. 2000, 122, 5968
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    • Trost, B.M.1    Patterson, D.E.2    Hembre, E.J.3
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    • For examples of palladium catalyzed DYKAT, see: (a) Trost, B. M.; Patterson, D. E.; Hembre, E. J. J. Am. Chem. Soc. 1999, 121, 10 834. (b) Trost, B. M.; Bunt, R. C.; Lemoine, R. C.; Calkins, T. L. J. Am. Chem. Soc. 2000, 122, 5968
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5968
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  • 33
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    • For enzyme catalyzed DYKAT of butenolides, see: van der Deen, H.; Cuiper, A. D.; Hof, R. P.; van Oeveren, A.; Feringa, B. L.; Kellogg, R. M. J. Am. Chem. Soc. 1996, 118, 3801. For a discussion of this racemization mechanism for allylic acetates, see: Grennber, H.; Langer, V.; Bäckvall, J. E. J. Chem. Soc., Chem. Commun. 1991, 1190 and references therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3801
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  • 34
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    • and references therein
    • For enzyme catalyzed DYKAT of butenolides, see: van der Deen, H.; Cuiper, A. D.; Hof, R. P.; van Oeveren, A.; Feringa, B. L.; Kellogg, R. M. J. Am. Chem. Soc. 1996, 118, 3801. For a discussion of this racemization mechanism for allylic acetates, see: Grennber, H.; Langer, V.; Bäckvall, J. E. J. Chem. Soc., Chem. Commun. 1991, 1190 and references therein.
    • (1991) J. Chem. Soc., Chem. Commun. , pp. 1190
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    • For examples of HF mediated Friedel-Crafts cyclizations of carboxylic acids see: (a) Chung, Y.-S.; Kruk, H.; Barizo, O. M.; Katz, M.; Lee-Ruff, E. J. Org. Chem. 1987, 52, 1284. (b) Konieczny, M.; Harvey, R. G. J. Org. Chem. 1979, 44, 2158. (c) Veeraraghavan, S.; Jostmeyer, S.; Myers, J.; Wiley Jr., J. C. J. Org. Chem. 1987, 52, 1355.
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  • 48
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    • For examples of HF mediated Friedel-Crafts cyclizations of carboxylic acids see: (a) Chung, Y.-S.; Kruk, H.; Barizo, O. M.; Katz, M.; Lee-Ruff, E. J. Org. Chem. 1987, 52, 1284. (b) Konieczny, M.; Harvey, R. G. J. Org. Chem. 1979, 44, 2158. (c) Veeraraghavan, S.; Jostmeyer, S.; Myers, J.; Wiley Jr., J. C. J. Org. Chem. 1987, 52, 1355.
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    • Konieczny, M.1    Harvey, R.G.2
  • 49
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    • For examples of HF mediated Friedel-Crafts cyclizations of carboxylic acids see: (a) Chung, Y.-S.; Kruk, H.; Barizo, O. M.; Katz, M.; Lee-Ruff, E. J. Org. Chem. 1987, 52, 1284. (b) Konieczny, M.; Harvey, R. G. J. Org. Chem. 1979, 44, 2158. (c) Veeraraghavan, S.; Jostmeyer, S.; Myers, J.; Wiley Jr., J. C. J. Org. Chem. 1987, 52, 1355.
    • (1987) J. Org. Chem. , vol.52 , pp. 1355
    • Veeraraghavan, S.1    Jostmeyer, S.2    Myers, J.3    Wiley J.C., Jr.4


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