N-methyl-(R)-3-(tert-butyl)-sulfinyl-1,4-dihydropyridine: a novel NADH model compound.
We have synthesized a novel chiral NADH model compound, N-methyl-(R)-3-(tert-butyl)-sulphinyl-1,4-dihydropyridine with high enantioselectivity and used it in the reduction of methyl benzoylformate, producing (S)-methyl mandelate in 95% ee. The absolute structure of its precursor, 3-(tert-butyl)sulfinyl pyridine, was determined by X-ray analysis.
Xie
Kun
K
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, PR China. wilma@mail.ustc.edu.cn
Liu
You-Cheng
YC
Cui
Yi
Y
Wang
Jian-Ge
JG
Fu
Yao
Y
Mak
Thomas C W
TC
D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D009243:NAD / Q000737:chemistry*; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000737:chemistry
D004095:Dihydropyridines; C523621:N-methyl-3-(tert-butyl)sulfinyl-1,4-dihydropyridine; D013454:Sulfoxides; D009243:NAD; C038806:1,4-dihydropyridine