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The tertiary phosphine- or amine-catalyzed addition of alcohols to terminal alkynoates is a well-established synthetic procedure: a) J. Inanaga, Y. Baba, T. Hanamoto, Chem. Lett. 1993, 241-243; b) for a version of this reaction under fluorous catalysis, see: M. Wende, R. Meier, J. A. Gladysz, J. Am. Chem. Soc. 2001, 123, 11490-11491; c) for a stoichiometric use of a tertiary amine, see: E. Winterfeldt, H. Prouss, Chem. Ber. 1966, 99, 450-457; d) for one synthetic application, see: M. Hirama, T. Oishi, H. Uehara, M. Inoue, M. Maruyama, H. Oguri, M. Satake, Science 2001, 294, 1904-1907.
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The tertiary phosphine- or amine-catalyzed addition of alcohols to terminal alkynoates is a well-established synthetic procedure: a) J. Inanaga, Y. Baba, T. Hanamoto, Chem. Lett. 1993, 241-243; b) for a version of this reaction under fluorous catalysis, see: M. Wende, R. Meier, J. A. Gladysz, J. Am. Chem. Soc. 2001, 123, 11490-11491; c) for a stoichiometric use of a tertiary amine, see: E. Winterfeldt, H. Prouss, Chem. Ber. 1966, 99, 450-457; d) for one synthetic application, see: M. Hirama, T. Oishi, H. Uehara, M. Inoue, M. Maruyama, H. Oguri, M. Satake, Science 2001, 294, 1904-1907.
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The tertiary phosphine- or amine-catalyzed addition of alcohols to terminal alkynoates is a well-established synthetic procedure: a) J. Inanaga, Y. Baba, T. Hanamoto, Chem. Lett. 1993, 241-243; b) for a version of this reaction under fluorous catalysis, see: M. Wende, R. Meier, J. A. Gladysz, J. Am. Chem. Soc. 2001, 123, 11490-11491; c) for a stoichiometric use of a tertiary amine, see: E. Winterfeldt, H. Prouss, Chem. Ber. 1966, 99, 450-457; d) for one synthetic application, see: M. Hirama, T. Oishi, H. Uehara, M. Inoue, M. Maruyama, H. Oguri, M. Satake, Science 2001, 294, 1904-1907.
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This fact rules out the possibility of thermodynamic formation of the acetylide ion by a direct acid-base reaction of the terminal alkynoate with the base. If this were the case, these basic amines would have been good or at least moderate catalysts for these reactions. They are not, and their deficient catalyst ability is explained by their kinetic incapability to trigger these cascade processes.
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62
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0345381993
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We have recently accomplished an expeditious one-pot synthesis of 5-substituted tetronic acids (4-hydroxy-5H-furan-2-one) by the controlled acid hydrolysis of 1,3-dioxolanes 2; see D. Tejedor, G. V. López, F. García-Tellado, J. J. Marrero-Tellado, P. de Armas, D. Terrero, J. Org. Chem. 2003, 68, 3363-3365.
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Terrero, D.6
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