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Selected examples: a) W. C. Agosta, J. Am. Chem. Soc. 1962, 84, 110-111;
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0001648959
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73349119478
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See the Supporting Information
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See the Supporting Information.
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28
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73349143107
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The increased temperatures required for these reactions, relative to related carbonyl ylide cycloadditions, may be due to the increased steric requirements of the allene relative to olefins and alkynes
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The increased temperatures required for these reactions, relative to related carbonyl ylide cycloadditions, may be due to the increased steric requirements of the allene relative to olefins and alkynes.
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29
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0025108625
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34
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73349094489
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We are defining endo to be the product with the CO 2R3 group anti to the oxo bridge, as proposed by Padwa in reference [11a
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3 group anti to the oxo bridge, as proposed by Padwa in reference [11a].
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35
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73349128851
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While this analysis was only performed on the structures shown in Figure 2, all of the isolated products had very similar spectral characteristics within each diastereomeric series
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While this analysis was only performed on the structures shown in Figure 2, all of the isolated products had very similar spectral characteristics within each diastereomeric series.
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37
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0000725878
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41
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73349108916
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We attempted to use Marshall's Pd-catalyzed carbonylation of propargylic mesylates (Ref. [15a]) in order to construct enantioenriched 2e. Unfortunately, in our hands this method produced (S)-2e with moderate enantiopurity (72% ee). Because the diastereomeric relationship between 5 and 7 (and 6and 8) would complicate the determination of the enantiomeric excess in the product, we prefer to employ allenes with higher enantiopurity.
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We attempted to use Marshall's Pd-catalyzed carbonylation of propargylic mesylates (Ref. [15a]) in order to construct enantioenriched 2e. Unfortunately, in our hands this method produced (S)-2e with moderate enantiopurity (72% ee). Because the diastereomeric relationship between 5 and 7 (and 6and 8) would complicate the determination of the enantiomeric excess in the product, we prefer to employ allenes with higher enantiopurity.
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