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See Experimental Section for generation of the free carbene.
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We have shown that varying the electronic nature of the catalyst can have an affect on reactivity and selectivity; see ref 4c.
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The exact mode of the epimerization is still under investigation.
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See Supporting Information for crystal structure data.
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For examples of the reverse Cope elimination mechanism of hydroxylamine additions, see ref 11.
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Further support for the intramolecular proton-transfer event was gained by conducting the reactions at various concentrations. Lowering the reaction concentration from 0.3 to 0.02 M increased the diastereoselectivity from 10:1 to 30:1. The reactions were monitored by GC analysis over the course of 24 h and the diastereoselectivity remained constant for each reaction, suggesting that a bimolecular event leads to a slight degradation of selectivity. However, it cannot be ruled out that higher concentration leads to a greater amount of epimerization.
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As mentioned above, it is also possible that the α-hydroxy-α- azolium anion adds to the Michael acceptor in concerted fashion, analogous to the reverse Cope elimination mechanism seen with hydroxylamine additions.
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4 salt, which was prepared according to general procedure, through a Gelman 0.45 μm filter.
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