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33644768766
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note
-
An atom-efficient decarboxylative modification of the Doebner-Knoevenagel reaction for the generation of α,β-unsaturated esters using malonic acid half esters in the presence of catalytic amounts of base has been published recently by List and co-workers: refs 3c,d.
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-
-
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46
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24944439544
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It is noteworthy that homoenolate III seems not to undergo any C-C bond formation as a competing electrophilic trapping event as it is observed for alkenyl substrates that can yield homolactones depending on the reaction conditions. Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873-3876.
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49
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0031037758
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Only low selectivities (E/Z < 1:4) are observed in the final protonation event of 1,2,4-triazole-substituted ethoxy allenolate: Katritzky, A. R.; Feng, D.; Lang, H. J. Org. Chem. 1997, 62, 715-720.
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50
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33644762585
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note
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For details, see Supporting Information.
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-
-
-
51
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0038049457
-
-
IMes·HCl is commercially available (1 g ≈ $40). For its preparation, see: Arduengo, A. J., III. U.S. Patent 5,077,414, 1991. Triazolium precatalyst 5 was prepared according to a known procedure: Enders, D.; Breuer, K.; Kallfass, U.; Balensiefer, T. Synthesis 2003, 1292-1295.
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Enders, D.1
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Balensiefer, T.4
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52
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33644746959
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note
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For an exemplary GC/MS of a crude reaction mixture (Table 1, entry 8), see Supporting Information.
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