title: Synthetic versatility in C-H oxidation: a rapid approach to differentiated diols and pyrans from simple olefins.
abstract: Conventionally, C-H oxidation reactions are used to install functional groups. The use of C-H oxidation to transform simple starting materials into highly versatile intermediates, which enable rapid access to a range of complex target structures, is a new area with tremendous potential in synthesis. Herein we report a Pd(II)/sulfoxide-catalyzed allylic C-H oxidation to form anti-1,4-dioxan-2-ones from homoallylic oxygenates. These versatile building blocks are rapidly elaborated to differentiated syn-1,2-diols, stereodefined amino-polyols, and syn-pyrans, structures ubiquitous in medicinally important complex molecules found in Nature. We also demonstrate that a C-H oxidation approach to the synthesis of these motifs is orthogonal and complementary to other state-of-the-art methods.
authors: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
authors: Paul E
authors: PE
authors: Gormisky
authors: M Christina
authors: MC
authors: White
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D006018:Glycols / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis*
chemical_list: D000475:Alkenes; D006018:Glycols; D011714:Pyrans; D010165:Palladium