Umpolung in 'Michael' Chemistry

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Abstract: The chemistry of enamine N-oxides has only ever been investigated twice since the dawn of modern organic synthesis. We are going to use these rare species to reverse the polarity of the intermediate in a classical example of a Michael (1,4-addition) reaction. This unprecedented change in polarity will allow the rapid synthesis of densely functionalized organic intermediates through the addition of two sequential nucleophiles. Chiral fragments (including amines, aminoacids, aminoalcohols, etc.) of use in natural product and advanced pharmaceutical synthesis will be prepared. The latter sector is one of the fastest growing in the world fine chemical market (~4 billion p.a. with growth of ~10% yr-1).