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Use of Magnesium Bisamides as Bases

A centerpiece of our reagent studies has been an investigation into the utility of magnesium bisamides, (R2N)2Mg, as alternatives to the widely used lithium amides, R2NLi, as strong bases in synthesis. In many instances these new reagents outperform existing methods and also have distinct advantages due to their simple preparation, low cost, and ease of use. The scheme above summarizes the use of these reagents in a set of benchmark reactions: (i) regioselective enolizations, (ii) stereoselective enolizations, (iii) aldol additions, and (iv) enantioselective deprotonations. For recent additons to this chemistry see: J. Am. Chem. Soc. 2006, 128, 13599.

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