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3). Various modes of addition were tried, including the use of special apparatus (see ref 18) for addition of cold solutions.
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We were alerted to the poor enantioselectivity of the allylation when X-ray analysis of a more advanced intermediate showed the material to be a racemate. See Supporting Information for structure and CCDC registry number.
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A small amount of the starting aldehyde was recovered, indicating that the aldehyde did not epimerize (by retro-Michael addition and Michael addition).
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For a mechanistically related method, see ref 10.
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We found this method more convenient than that reported in the literature
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70349457452
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note
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2) were unsuccessful and gave complex mixtures.
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70349454879
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2P(O)Cl.
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102
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0141507075
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For a related pivaloate that is stable to chromatography, see ref 44. For related isolable acetates, see: (a)
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For a related pivaloate that is stable to chromatography, see ref 44. For related isolable acetates, see: (a) Dransfield, P. J.; Gore, P. M.; Prokes, I.; Shipman, M.; Slawin, A. M. Z. Org. Biomol. Chem. 2003, 1, 2723-2733.
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105
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70349444322
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note
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See Supporting Information.
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107
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33845551642
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Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424-2426.
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70349461818
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note
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See Supporting Information for the preparation and subsequent Claisen rearrangement, in the presence of butyl vinyl ether, of 18 and 20a.
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