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28044453908
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For a recent review on Negishi-type couplings, see
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For a recent review on Negishi-type couplings, see: Negishi, E.; Hu, Q.; Huang, Z.; Qian, M.; Wang, G. Aldrichimica Acta 2005, 38, 71.
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31
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34547929867
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Other conditions explored were PPh3/I2/imidazole; PPh3/CI4; NaI/ heat; and MsCl/NaI.
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Other conditions explored were PPh3/I2/imidazole; PPh3/CI4; NaI/ heat; and MsCl/NaI.
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33
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4944225467
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35
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34547935703
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The enantiomeric excess of this reaction was determined by Mosher ester analysis of the α-hydroxyester 18
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The enantiomeric excess of this reaction was determined by Mosher ester analysis of the α-hydroxyester 18.
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36
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42
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34547960669
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The yield of alkyllithium species 20 was determined by trapping 20 with amide 5 and isolation of the ketone 21 thus formed.
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The yield of alkyllithium species 20 was determined by trapping 20 with amide 5 and isolation of the ketone 21 thus formed.
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43
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34547939068
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For reviews about the cyclization of usaturated organolithiums, see: a, Pergamon Press: New York, New York
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For reviews about the cyclization of usaturated organolithiums, see: (a) Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon Press: New York, New York, 2002; Vol. 3, pp 293-335.
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Clayden, J.1
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46
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34547948111
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Because the amide 5 had an ee of 80%, the coupling yielded ∼10% of the (8R)-epimer of ketone 21, which could be separated by column chromatography at this stage.
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Because the amide 5 had an ee of 80%, the coupling yielded ∼10% of the (8R)-epimer of ketone 21, which could be separated by column chromatography at this stage.
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47
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34547941012
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The relative stereochemistry was confirmed after converting the alcohol into an acetonide by NOESY NMR spectroscopy see Supporting Information
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The relative stereochemistry was confirmed after converting the alcohol into an acetonide by NOESY NMR spectroscopy (see Supporting Information).
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