SmI(2)-promoted oxidation of aldehydes in the presence of electron-rich heteroatoms.
[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.
Smith
Amos B
AB
Department of Chemistry, Laboratory for Research on the Structure of Matter, Monell Chemical Senses Center, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Lee
Dongjoo
D
Adams
Christopher M
CM
Kozlowski
Marisa C
MC
D000447:Aldehydes / Q000737:chemistry*; D004583:Electrons; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000447:Aldehydes; D004952:Esters; D007659:Ketones