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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 (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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