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• W2078429567 abstract "In an effort to understand and enhance the stereochemical outcome of the MOM-ether directed rearrangement of allylic trichloroacetimidates we have investigated various reaction conditions for this process. A range of Pd(II) and other metal catalysts have been shown to effectively catalyse the rearrangement providing the subsequent allylic amides in high selectivity (up to 11 : 1 ratio of diastereomers). The replacement of THF as a solvent in this reaction with non-coordinating solvents such as toluene has led to an enhancement of the directing effect resulting in a significant increase in the diastereoselective outcome (15 : 1 ratio). The reaction was also carried out for the first time, using a highly coordinating ionic solvent which disrupts binding of the Pd(II)-catalyst to the MOM-ether yielding the allylic amide in only moderate diastereoselectivity. These results provide further evidence for the ether directed aza-Claisen rearrangement of allylic trichloroacetimidates." @default.
• W2078429567 created "2016-06-24" @default.
• W2078429567 creator A5001024841 @default.
• W2078429567 creator A5033695188 @default.
• W2078429567 date "2006-01-01" @default.
• W2078429567 modified "2023-10-03" @default.
• W2078429567 title "Scope and limitations of ether-directed, metal-catalysed aza-Claisen rearrangements; improved stereoselectivity using non-coordinating solvents" @default.
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• W2078429567 doi "https://doi.org/10.1039/b607014k" @default.
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