Literature DB >> 17851400

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

Kun Xie1, You-Cheng Liu, Yi Cui, Jian-Ge Wang, Yao Fu, Thomas C W Mak.   

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.

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Year:  2007        PMID： 17851400      PMCID： PMC6149371          DOI： 10.3390/12030415

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  3 in total

1.  New general sulfinylating process for asymmetric synthesis of enantiopure sulfinates and sulfoxides.

Authors:  Bruce Z Lu; Fuqiang Jin; Yongda Zhang; Xinhe Wu; Stephen A Wald; Chris H Senanayake
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

2.  Letter: Reduction by a model of NAD(P)H. Effect of metal ion and stereochemistry on the reduction of alpha-keto esters by 1,4-dihydronicotinamide derivatives.

Authors:  Y Onishi; M Kagami; A Ono
Journal:  J Am Chem Soc       Date:  1975-08-06       Impact factor: 15.419

3.  N-tert-butanesulfinyl imines: versatile intermediates for the asymmetric synthesis of amines.

Authors:  Jonathan A Ellman; Timothy D Owens; Tony P Tang
Journal:  Acc Chem Res       Date:  2002-11       Impact factor: 22.384
  3 in total
  3 in total

1.  Amine-functionalized graphene oxide nanosheets (AFGONs): an efficient bifunctional catalyst for selective formation of 1,4-dihydropyridines, acridinediones and polyhydroquinolines.

Authors:  Prasun Choudhury; Pranab Ghosh; Basudeb Basu
Journal:  Mol Divers       Date:  2019-04-06       Impact factor: 2.943

2.  A new type of NADH model compound: synthesis and enantioselective reduction of benzoylformates to the corresponding mandelates.

Authors:  Jia Zhao; Nai-Xing Wang; Wu-Wei Wang; Gui-Xia Wang; Yan-Hong Liu; Li Li; Jin-Lan Yu; Xin-Liang Tang
Journal:  Molecules       Date:  2007-05-11       Impact factor: 4.411

Review 3.  1,4-Dihydropyridine Derivatives: Dihydronicotinamide Analogues-Model Compounds Targeting Oxidative Stress.

Authors:  Astrida Velena; Neven Zarkovic; Koraljka Gall Troselj; Egils Bisenieks; Aivars Krauze; Janis Poikans; Gunars Duburs
Journal:  Oxid Med Cell Longev       Date:  2016-01-06       Impact factor: 6.543
  3 in total

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