Reduction of activated carbonyl groups by alkyl phosphines: formation of alpha-hydroxy esters and ketones.
Reduction of activated carbonyl groups such as alpha-keto esters, benzils, 1,2-cyclohexanedione, and alpha-ketophosphonates by alkyl phosphines afforded the corresponding alpha-hydroxy esters or ketones in good to excellent yields in THF at room temperature. The mechanism of the proton transfer and intramolecular hydrolysis has been studied on the basis of deuterium and 18O labeling experiments.
Zhang
Wen
W
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Shi
Min
M
D004952:Esters / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010658:Phenylglyoxal / Q000031:analogs & derivatives / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*
D004952:Esters; D007659:Ketones; D010720:Phosphines; D010658:Phenylglyoxal; C006697:benzil