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N-Methyl-(R)-3-(tert-Butyl)-Sulfinyl-1,4-Dihydropyridine: A Novel NADH Model Compound
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P.R. China
College of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P.R. China
Department of Chemistry, Luoyang Normal University, Luoyang, Henan, 471022, P.R. China
Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, P.R. China
* Author to whom correspondence should be addressed.
Received: 25 February 2007; in revised form: 7 March 2007 / Accepted: 7 March 2007 / Published: 12 March 2007
Abstract: 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.
Keywords: NADH model compound; chiral; sulfoxide; dihydropyridine; synthesis
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MDPI and ACS Style
Xie, K.; Liu, Y.-C.; Cui, Y.; Wang, J.-G.; Fu, Y.; Mak, T.C. N-Methyl-(R)-3-(tert-Butyl)-Sulfinyl-1,4-Dihydropyridine: A Novel NADH Model Compound. Molecules 2007, 12, 415-422.
Xie K, Liu Y-C, Cui Y, Wang J-G, Fu Y, Mak TC. N-Methyl-(R)-3-(tert-Butyl)-Sulfinyl-1,4-Dihydropyridine: A Novel NADH Model Compound. Molecules. 2007; 12(3):415-422.
Xie, Kun; Liu, You-Cheng; Cui, Yi; Wang, Jian-Ge; Fu, Yao; Mak, Thomas C. 2007. "N-Methyl-(R)-3-(tert-Butyl)-Sulfinyl-1,4-Dihydropyridine: A Novel NADH Model Compound." Molecules 12, no. 3: 415-422.