N-methyl-(R)-3-(tert-butyl)-sulfinyl-1,4-dihydropyridine: a novel NADH model compound

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)sulfi...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2007-03, Vol.12 (3), p.415-422
Main Authors: Xie, Kun, Liu, You-Cheng, Cui, Yi, Wang, Jian-Ge, Fu, Yao, Mak, Thomas C W
Format: Article
Language:English
Subjects:
chiral
dihydropyridine
Dihydropyridines - chemical synthesis
Dihydropyridines - chemistry
Models, Molecular
NAD - chemistry
NADH model compound
sulfoxide
Sulfoxides - chemical synthesis
Sulfoxides - chemistry
synthesis
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/12030415