title: SmI(2)-promoted oxidation of aldehydes in the presence of electron-rich heteroatoms.
abstract: [reaction: see text] The Evans-Tishchenko reaction provides an efficient and practical solution for the oxidation of aldehydes possessing sensitive electron-rich heteroatoms to the corresponding esters. Careful selection of the sacrificial beta-hydroxy ketone provides considerable subsequent flexibility to access the desired carboxylic acid.
authors.affiliation: Department of Chemistry, Laboratory for Research on the Structure of Matter, Monell Chemical Senses Center, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
authors.forename: Dongjoo
authors.initials: D
authors.lastname: Lee
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Adams
authors.forename: Marisa C
authors.initials: MC
authors.lastname: Kozlowski
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D004583:Electrons; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D004952:Esters; D007659:Ketones