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0003483137
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33847085179
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a) L. S. Hegedus, W. H. Darlington, C. E. Russell, J. Org. Chem. 1980, 45, 5193-5196;
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31
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0001041487
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In contrast, the much less reactive silylketene acetals preferentially attack the allylic position: a) J. Tsuji, K. Takahashi, I. Minami, I. Shimizu, Tetrahedron Lett. 1984, 25, 4783-4786;
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34
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33747551758
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note
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Instead of the carbonate 3, the corresponding acetate or benzoate can be used as well. With the more reactive carbonates, the yields and selectivities are usually better. To avoid transesterifications by the liberated ethylate the tert-butyl ester should be used.
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-
-
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35
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33747522633
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note
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2 can be used as well. However, distinctly worse yields and selectivities are observed. In reactions of the lithium enolates (without addition of a chelating metal salt) N-allylated products can be isolated in addition to C-allylated products.
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-
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38
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33747561506
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-
note
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However, a partial cleavage of the crotyl ester occurs.
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-
-
-
39
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33747561178
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-
note
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If the Pd-catalyzed allylation is carried out in the presence of LDA, product mixtures are usually formed due to the partial cleavage of the crotyl ester.
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