7.07 α-Oxygenation of Carbonyl Compounds
2014 (English)In: Comprehensive Organic Synthesis II (Second Edition) / [ed] Paul Knochel and Gary A. Molander, Amsterdam: Oxford: Elsevier , 2014, 2nd, 213-241 p.Chapter in book (Refereed)
Abstract The chapter describes synthetically useful strategies for α-oxygenation of carbonyl compounds, with special emphasis on recent methods for catalytic and asymmetric reactions. The oxidation of enolates, enols, enol ethers, and α,β-unsaturated compounds is discussed in detail. Classical oxidation reagents like metal oxides, molecular oxygen, peroxides, and peracids are covered, with asymmetric dihydroxylation of enol ethers giving the highest enantioselectivities together with organocatalytic methods using peroxides. Oxaziridines, nitrosoarenes, and hypervalent iodine compounds are more recently developed α-oxygenation alternatives that allow metal-free oxidations under mild conditions. The combination of nitrosoarenes with organocatalysis is currently the best method for enantioselective α-oxygenations. The area of asymmetric α-oxygenations with hypervalent iodine compounds is currently under development, and high enantioselectivities have only been achieved in intramolecular reactions and epoxidations.
Place, publisher, year, edition, pages
Amsterdam: Oxford: Elsevier , 2014, 2nd. 213-241 p.
Acetoxylation, Asymmetric synthesis, Dihydroxylation, Epoxidation, Hydroxylation, Hypervalent iodine, Organocatalysis, Oxidation, Tosyloxylation
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-109695DOI: 10.1016/B978-0-08-097742-3.00708-4ISBN: 978-0-08-097743-0OAI: oai:DiVA.org:su-109695DiVA: diva2:766476