Umpolung in 'Michael' Chemistry
Lead Research Organisation:
University of Nottingham
Department Name: Sch of Chemistry
Abstract
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).
Organisations
People |
ORCID iD |
| S Woodward (Principal Investigator) |
Publications
Bernier D
(2008)
Improved procedure for the synthesis of enamine N-oxides.
in The Journal of organic chemistry
Bernier D
(2009)
Properties, Preparation and Synthetic Uses of Amine N -Oxides. An Update
in Organic Preparations and Procedures International
Glynn D
(2008)
Microwave acceleration in DABAL-Me3-mediated amide formation
in Tetrahedron Letters
Shannon J
(2007)
Direct asymmetric catalytic 1,2-addition of RZnX to aldehydes promoted by AlMe3 and reversal of expected stereochemistry.
in Chemical communications (Cambridge, England)
Wefelscheid UK
(2009)
Rearrangement of beta-chloro N-oxides to hydroxylamines: opening of the oxazetidinium intermediate by different nucleophiles.
in The Journal of organic chemistry