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The reaction of lithium enolate (R)-8 (1.0 equiv.) and N-(tertbutoxycarbonyl) benzenemethanimine (1.5 equiv.) obtained in situ from the corresponding carbamoyl sulfone at -80 °C in THF/HMPA (85:15) yielded an inseparable 2.8:1 mixture of two compounds whose structures have not yet been clarified. A. Battaglia, unpublished results.
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The reaction of lithium enolate (R)-8 (1.0 equiv.) and N-(tertbutoxycarbonyl) benzenemethanimine (1.5 equiv.) obtained in situ from the corresponding carbamoyl sulfone at -80 °C in THF/HMPA (85:15) yielded an inseparable 2.8:1 mixture of two compounds whose structures have not yet been clarified. A. Battaglia, unpublished results.
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For recent applications of our protocol, see: a
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55
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53749091734
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This approach is probably preferred to avoid any repulsion of the (R)-configured anomeric hydrogen atom of the rigid sugar moiety with the methyl substituent of the enolate. In this approach, this hydrogen points towards the plane of the enolate
-
This approach is probably preferred to avoid any repulsion of the (R)-configured anomeric hydrogen atom of the rigid sugar moiety with the methyl substituent of the enolate. In this approach, this hydrogen points towards the plane of the enolate.
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