Reversible Enolization of β-Amino Carboxamides by Lithium Hexamethyldisilazide
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https://figshare.com/articles/dataset/Reversible_Enolization_of_Amino_Carboxamides_by_Lithium_Hexamethyldisilazide/3290272
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资源简介：
The enolization of β-amino carboxamides by lithium hexamethyldisilazide (LiHMDS) in THF/toluene and subsequent diastereoselective alkylation with CH3I are reported. In situ IR spectroscopic studies
reveal that β-amino carboxamides coordinate to LiHMDS at −78 °C before enolization. Comparison with
structurally similar carboxamides suggests that the β-amino group promotes the enolization. IR spectroscopic
studies also show that the enolization is reversible. Efficient trapping of the enolate by CH3I affords full
conversion to products. 6Li and 15N NMR spectroscopic studies reveal that lithium enolate−LiHMDS mixed
dimers and trimers as well as a homoaggregated enolate are formed during the reaction. At ambient
temperature, racemization of the β-position through a putative reversible Michael addition was observed.
创建时间：
2016-05-06
