Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
J Am Chem Soc. 2011 Jun 8;133(22):8432-5. doi: 10.1021/ja201873d. Epub 2011 May 16.
The combination of Fe(OTf)(2) and novel phenanthroline ligands enables the catalytic asymmetric epoxidation of acyclic β,β-disubstituted enones, which have been a heretofore inaccessible substrate class. The reaction provides highly enantioenriched α,β-epoxyketones (up to 92% ee) that can be further converted to functionalized β-ketoaldehydes with an all-carbon quaternary center.
Fe(OTf)(2)与新型菲咯啉配体的组合实现了环状β,β-二取代烯酮的催化不对称环氧化，而这类底物在此前是难以获得的。该反应提供了高对映选择性的α,β-环氧酮（高达 92%ee），其可以进一步转化为具有全碳季碳中心的官能化的β-酮醛。
