An efficient and general approach to beta-functionalized ketones.
[structure: see text]. The oxidation of selected anions (N3-, SCN-, I-, and Br-) by ceric ammonium nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides a novel approach to beta-functionalized ketones. The protocol has a number of advantages including short reaction times, ease of reagent handling, and mild, neutral reaction conditions. Overall, this method provides an alternative pathway to important starting materials and intermediates in organic synthesis.
Jiao
Jingliang
J
Department of Chemistry, Lehigh University, Bethlehem, PA 18015, USA.
Nguyen
Larry X
LX
Patterson
Dennis R
DR
Flowers
Robert A
RA
D000838:Anions / Q000737:chemistry; D002563:Cerium / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry
D000838:Anions; D003521:Cyclopropanes; D007659:Ketones; D020005:Propanols; D002563:Cerium; C004653:ceric ammonium nitrate