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Molecules 2007, 12(3), 415-422; doi:10.3390/12030415

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 / Revised: 7 March 2007 / Accepted: 7 March 2007 / Published: 12 March 2007
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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 NADH model compound; chiral; sulfoxide; dihydropyridine; synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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