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Volumn 18, Issue 23, 1999, Pages 4742-4746

Ruthenium-catalyzed allylic substitution of cyclic allyl carbonates with nucleophiles. Stereoselectivity and scope of the reaction

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EID: 0000683254     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990533k     Document Type: Article
Times cited : (95)

References (77)
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    • and references therein
    • For a recent example, see: (a) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. (b) Suzuki, N.; Kondo, T.; Mitsudo, T. Organometallics 1998, 17, 766. (c) Kondo, T.; Uenoyama, S.; Fujita, K.; Mitsudo, T. J. Am. Chem. Soc. 1999, 121, 482. (d) Mitsudo, T.; Suzuki, T.; Zhang, S.-W.; Imai, D.; Fujita, K.; Manabe, T.; Shiotsuki, M.; Watanabe, Y.; Wada, K.; Kondo, T. J. Am. Chem. Soc. 1999, 121, 1839 and references therein. For a review, see: Naota, T.; Takaya, H.; Murahashi, S. Chem. Rev. 1998, 98, 2599.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1839
    • Mitsudo, T.1    Suzuki, T.2    Zhang, S.-W.3    Imai, D.4    Fujita, K.5    Manabe, T.6    Shiotsuki, M.7    Watanabe, Y.8    Wada, K.9    Kondo, T.10
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    • and references therein
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    • The effect of the concentration of CpRuCl(cod) catalyst (5, 10, 25, and 50 mol %) was also examined in the reaction of cis-1e with 2a The beat stereoselectivity of product 3g was observed in eq 2 (5 mol % CpRuCl(cod), cis-3g/trans-3g = 95/5). While the increase of the concentration of CpRuCl(cod) catalyst slightly decreased the stereoselectivity of 3g, the stereoselectivity was constant in the range from 10 mol % to 50 mol % CpRuCl(cod) catalyst (10 mol %, cis-3g/trans-3g = 86/14; 25 mol %, cis-3g/trans-3g = 88/12; 50 mol %, cis-3g/trans-3g = 87/13). For a related reference, see: Ward, Y. D.; Villanueva, L. A.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 897.
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    • note
    • Since no reaction occurred between Cp*RuCl(cod) and an allylic carbonate, trans-1e, under the stoichiometric reaction conditions, the reaction with a more reactive allylic halide, trans-6a, was examined.
  • 47
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    • 6-arene)ruthenium(II) complexes by dehydrogenation of cyclohexadienes with ruthenium(III) trichloride has been reported: Bennet, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233.
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    • note
    • w = 0.060, GOF = 1.04.
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    • For a mechanism with double inversion of configuration in palladium-catalyzed allylic alkylation reactions, see: (a) Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1983, 105, 7767. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 107. (c) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723. (d) Fiaud, J.-C.; Legros, J.-Y. J. Org. Chem. 1987, 52, 1907.
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    • For a mechanism with double inversion of configuration in palladium-catalyzed allylic alkylation reactions, see: (a) Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1983, 105, 7767. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 107. (c) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723. (d) Fiaud, J.-C.; Legros, J.-Y. J. Org. Chem. 1987, 52, 1907.
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    • For a mechanism with double inversion of configuration in palladium-catalyzed allylic alkylation reactions, see: (a) Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1983, 105, 7767. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 107. (c) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723. (d) Fiaud, J.-C.; Legros, J.-Y. J. Org. Chem. 1987, 52, 1907.
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    • For a mechanism with double inversion of configuration in palladium-catalyzed allylic alkylation reactions, see: (a) Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1983, 105, 7767. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 107. (c) Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723. (d) Fiaud, J.-C.; Legros, J.-Y. J. Org. Chem. 1987, 52, 1907.
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    • A mechanism with double retention of configuration is unlikely in the present reaction, but cannot be completely ruled out: (a) Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670. (b) Dvořák, D.; Starý, I.; Kočovský, P. J. Am. Chem. Soc. 1995, 117, 6130.
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    • A mechanism with double retention of configuration is unlikely in the present reaction, but cannot be completely ruled out: (a) Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670. (b) Dvořák, D.; Starý, I.; Kočovský, P. J. Am. Chem. Soc. 1995, 117, 6130.
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