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

N-Methyl-(R)-3-(tert-Butyl)-Sulfinyl-1,4-Dihydropyridine: A Novel NADH Model Compound

Kun Xie 1 email, You-Cheng Liu 1,* email, Yi Cui 1 email, Jian-Ge Wang 3 email, Yao Fu 1  and Thomas CW Mak 4 email
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; in revised form: 7 March 2007 / Accepted: 7 March 2007 / Published: 12 March 2007
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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.

AMA Style

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.

Chicago/Turabian Style

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.

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