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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

1,* , 1
1 and 4
1 Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P.R. China 2 College of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P.R. China 3 Department of Chemistry, Luoyang Normal University, Luoyang, Henan, 471022, P.R. China 4 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


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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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