title: A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs.
abstract: Chiral oxygenated molecules are pervasive in natural products and medicinal agents; however, their chemical syntheses often necessitate numerous, wasteful steps involving functional group and oxidation state manipulations. Herein a strategy for synthesizing a readily diversifiable class of chiral building blocks, allylic alcohols, through sequential asymmetric C-H activation/resolution is evaluated against the state-of-the-art. The C-H oxidation routes' capacity to strategically introduce oxygen into a sequence and thereby minimize non-productive manipulations is demonstrated to effect significant decreases in overall step-count and increases in yield and synthetic flexibility.
authors.affiliation: Department of Pathology and Laboratory Medicine, University of Pennsylvania School of Medicine Philadelphia, PA 19104, USA.
authors.forename: Dustin J
authors.initials: DJ
authors.lastname: Covell
authors.affiliation: Department of Chemistry, Roger Adams Laboratory, University of Illinois Urbana, IL 61801, USA.
authors.forename: M Christina
authors.initials: MC
authors.lastname: White
keywords: Allylic alcohols; Allylic oxidation; C–H oxidation; Enantioselective; Palladium; Sulfoxide