Eu(fod)3-catalyzed rearrangement of allylic methoxyacetates

Journal of the American Chemical Society

Volumn 118, Issue 46, 1996, Pages 11690-11691

  Shull, Brian K ^a,b   Sakai, Takashi ^a   Koreeda, Masato ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b Glycosyn Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029862760     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962718d     Document Type: Article

References (36)

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18. For reviews, see: (a) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (b) Hegedus, L. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, pp 551-569. (c) McDaniel, K. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 12, pp 601-622. (d) Tsuji, J. Palladium Reagent and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1995; pp 399-404. For leading references, see: (e) Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 321. (f) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (g) Panek, J. S.; Yang, M.; Solomon, J. S. J. Org. Chem. 1993, 58, 1003. (h) Clayden, J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1993, 2913.
19. For reviews, see: (a) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (b) Hegedus, L. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, pp 551-569. (c) McDaniel, K. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 12, pp 601-622. (d) Tsuji, J. Palladium Reagent and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1995; pp 399-404. For leading references, see: (e) Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 321. (f) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (g) Panek, J. S.; Yang, M.; Solomon, J. S. J. Org. Chem. 1993, 58, 1003. (h) Clayden, J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1993, 2913.
20. For reviews, see: (a) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (b) Hegedus, L. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, pp 551-569. (c) McDaniel, K. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 12, pp 601-622. (d) Tsuji, J. Palladium Reagent and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1995; pp 399-404. For leading references, see: (e) Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 321. (f) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (g) Panek, J. S.; Yang, M.; Solomon, J. S. J. Org. Chem. 1993, 58, 1003. (h) Clayden, J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1993, 2913.
21. For reviews, see: (a) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (b) Hegedus, L. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, pp 551-569. (c) McDaniel, K. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 12, pp 601-622. (d) Tsuji, J. Palladium Reagent and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1995; pp 399-404. For leading references, see: (e) Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 321. (f) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (g) Panek, J. S.; Yang, M.; Solomon, J. S. J. Org. Chem. 1993, 58, 1003. (h) Clayden, J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1993, 2913.
22. For reviews, see: (a) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (b) Hegedus, L. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, pp 551-569. (c) McDaniel, K. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 12, pp 601-622. (d) Tsuji, J. Palladium Reagent and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1995; pp 399-404. For leading references, see: (e) Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 321. (f) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (g) Panek, J. S.; Yang, M.; Solomon, J. S. J. Org. Chem. 1993, 58, 1003. (h) Clayden, J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1993, 2913.
23. For reviews, see: (a) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (b) Hegedus, L. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, pp 551-569. (c) McDaniel, K. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 12, pp 601-622. (d) Tsuji, J. Palladium Reagent and Catalysts: Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1995; pp 399-404. For leading references, see: (e) Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 321. (f) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (g) Panek, J. S.; Yang, M.; Solomon, J. S. J. Org. Chem. 1993, 58, 1003. (h) Clayden, J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1993, 2913.
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29. 10
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36. The propensity of the Eu for this methoxyacetoxy system is to the extent that silica gel chromatography does not rid the substrate of all of the Eu (the fod ligand is lost). Interestingly, even Kugelrohr distillation of the methoxyacetates presents the same problem. The Eu reagent is best removed by washing the ether solution of the product with a 2.5% ethylenebis-(oxyethylenenitrilo)tetraacetic acid (EGTA) slurry.