Chemical and Pharmaceutical Bulletin p. 616 - 618 (1990)
Update date:2022-09-26
Topics:
Tanaka
Kimura
Chen
Kawamoto
Yoneda
A nonenzymatic asymmetric reduction of ethyl benzoylformate with an achiral 1,5-dihydro-5-deazaflavin derivative in chiral media was investigated as a model system for reduced nicotinamide adenine dinucleotide (phosphate)-dependent dihydrogenase. The chiral media include chiral nuclear magnetic resonance shift reagent, chiral Lewis acid, and a combination of metal ion and chiral ligand (additive). Of these reductions, a substantial asymmetric induction was observed in the presence of tris-[3-(heptafluoropropylhydroxymethylene)(+)-camphorato]europium to give ethyl mandelate possessing predominantly S-configuration, in an optical yield of 24 to 36%. These values are among the highest so far reported in nonenzymatic reduction of ethyl benzoylformate with a 5-deazaflavin model. The discrimination of the prochiral face of the carbonyl compound was effective even when a catalytic amount of the chiral shift reagent was employed.
View Moresuzhou chukai pharmateach co,.ltd
Contact:86-512-88812511
Address:Building 3, Wujiang Scientific Innovation Park, 2358 Changan Rd, Wujiang 215200, Jiangsu Province, P. R. China
website:http://www.enbridgepharm.com
Contact:+86-510-83591909
Address:Huishan Zone, Wuxi City, Jiangsu Province, P.R.China
Tianjin Ingenochem Technology Co.,Ltd
Contact:+86-22-23677060
Address:Hitech Green Industry Park K2-9-602, Nankai district
Contact:+86-511-88790000
Address:338 North Yushan Rd, Zhenjiang, Jiangsu 212016
Contact:+86-25-85281586
Address:13F,Bld2#,South of Longpan Road
Doi:10.1039/c0cc04546b
(2011)Doi:10.1039/ft9908601549
(1990)Doi:10.1002/anie.201007733
(2011)Doi:10.3390/molecules21080988
(2016)Doi:10.1021/ic1023345
(2011)Doi:10.1016/j.tet.2011.02.025
(2011)