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Part I: Development of a General and Efficient Alternative to the Baylis-Hillman Reaction; Part II: Asymmetric Alkylation via Primary Activated Hydrazones
- Abstract:
Part I. Acryloyl chlorides, aldehydes, and lithium thiophenolate participate in a four-component direct aldol addition via in situ-derived thioester enolates, which can then be followed by oxidative-elimination to give the corresponding β’-hydroxy-α,β- unsaturated carbonyl compounds. This two-step procedure is rapid, efficient, and generally applicable, even to β-substituted acryloyl chlorides, making it an attractive alternative to the Baylis-Hillman reaction and of even broader scope.
Part II. Primary activated acyl hydrazide chiral auxiliaries can be used in the regio- and stereoselective α-alkylation of aldehydes and ketones. These auxiliaries offer more structural variation than the widely used dialkyl hydrazone auxiliaries (SAMP/RAMP), and hydrozone formation is facile in comparison to dialkyl hydrazone formation.
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