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There have been some reports on the catalytic asymmetric aza-Diels-Alder reactions for the construction of 2-aryl-2,3-dihydro-4-pyridones, see: (a) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979.
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Alkylzinc reagents (e.g., diethyl zinc) have been widely used in the copper-catalyzed asymmetric 1,4-addition reactions. For an overview, see: Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: New York, 1999; Chapter 31.1.
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2442684913
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note
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The yield could not be further improved by changing the stoichiometry of PhB(OH)2, the reaction temperature, or the reaction time.
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36
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38
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2442687412
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note
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The absolute configuration of the 1,4-adducts was assigned to be (R), based on the optical rotation of compound 3 in eq 2 (see Supporting Information).
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39
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2442689862
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note
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Under our standard conditions, alkyl- or alkenylzinc reagents are not suitable nucleophiles.
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