Literature DB >> 20890455

Spiroborate esters in the borane-mediated asymmetric synthesis of pyridyl and related heterocyclic alcohols.

Viatcheslav Stepanenko1, Melvin De Jesús, Wildeliz Correa, Irisbel Guzmán, Cindybeth Vázquez, Lymaris Ortiz, Margarita Ortiz-Marciales.   

Abstract

The effectiveness of several spiroborate ester catalysts was investigated in the asymmetric borane reduction of 2-, 3-, 4-acetylpyridines under different reaction conditions. Highly enantiomerically enriched 1-(2-, 3- and 4-pyridyl)ethanols and 1-(heterocyclic)ethanols were obtained using 1 to 10% catalytic loads of the spiroborate 5 derived from diphenylprolinol and ethylene glycol.

Entities:  

Year:  2007        PMID： 20890455      PMCID： PMC2948488          DOI： 10.1016/j.tetasy.2007.10.044

Source DB:  PubMed          Journal:  Tetrahedron Asymmetry        ISSN： 0957-4166


  5 in total

1.  Enzyme-catalyzed enantioselective diaryl ketone reductions.

Authors:  Matthew D Truppo; David Pollard; Paul Devine
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

2.  The "reverse-tethered" ruthenium (II) catalyst for asymmetric transfer hydrogenation: further applications.

Authors:  David J Morris; Aidan M Hayes; Martin Wills
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

3.  Novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. A structure-activity relationship investigation.

Authors:  Gabriella De Martino; Giuseppe La Regina; Alessandra Di Pasquali; Rino Ragno; Alberto Bergamini; Chiara Ciaprini; Anna Sinistro; Giovanni Maga; Emmanuele Crespan; Marino Artico; Romano Silvestri
Journal:  J Med Chem       Date:  2005-06-30       Impact factor: 7.446

4.  Role of NaBH(4) stabilizer in the oxazaborolidine-catalyzed asymmetric reduction of ketones with BH(3-)THF.

Authors:  Shawn M Nettles; Karl Matos; Elizabeth R Burkhardt; Dave R Rouda; Joseph A Corella
Journal:  J Org Chem       Date:  2002-05-03       Impact factor: 4.354

5.  Asymmetric synthesis of primary amines via the spiroborate-catalyzed borane reduction of oxime ethers.

Authors:  Xiaogen Huang; Margarita Ortiz-Marciales; Kun Huang; Viatcheslav Stepanenko; Francisco G Merced; Angel M Ayala; Wildeliz Correa; Melvin De Jesús
Journal:  Org Lett       Date:  2007-03-31       Impact factor: 6.005
  5 in total
  8 in total

1.  CATALYTIC ENANTIOSELECTIVE BORANE REDUCTION OF BENZYL OXIMES: PREPARATION OF (S)-1-PYRIDIN-3-YL-ETHYLAMINE BIS HYDROCHLORIDE.

Authors:  Kun Huang; Margarita Ortiz-Marciales; David Hughes
Journal:  Organic Synth       Date:  2010-01-01

2.  Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols.

Authors:  Kun Huang; Haiyang Wang; Viatcheslav Stepanenko; Melvin De Jesús; Carilyn Torruellas; Wildeliz Correa; Margarita Ortiz-Marciales
Journal:  J Org Chem       Date:  2011-02-04       Impact factor: 4.354

3.  SYNTHESIS OF SPIROBORATE ESTERS FROM 1,2-AMINOALCOHOLS, ETHYLENE GLYCOL AND TRIISOPROPYL BORATE: PREPARATION OF (S)-1-(1,3,2-DIOXABOROLAN-2-YLOXY)-3-METHYL-1,1-DIPHENYLBUTAN-2-AMINE.

Authors:  Viatcheslav Stepanenko; Kun Huang; Margarita Ortiz-Marciales; David Hughes
Journal:  Organic Synth       Date:  2010

4.  Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman and thiochroman containing ketones.

Authors:  Viatcheslav Stepanenko; Melvin De Jesús; Wildeliz Correa; Lorianne Bermúdez; Cindybeth Vázquez; Irisbel Guzmán; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2009-12-11

5.  A practical and efficient route for the highly enantioselective synthesis of mexiletine analogues and novel beta-thiophenoxy and pyridyl ethers.

Authors:  Kun Huang; Margarita Ortiz-Marciales; Viatcheslav Stepanenko; Melvin De Jesús; Wildeliz Correa
Journal:  J Org Chem       Date:  2008-08-09       Impact factor: 4.354

6.  Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: application to the synthesis of nicotine analogues.

Authors:  Kun Huang; Francisco G Merced; Margarita Ortiz-Marciales; Héctor J Meléndez; Wildeliz Correa; Melvin De Jesús
Journal:  J Org Chem       Date:  2008-05-01       Impact factor: 4.354

7.  Spiroborate ester-mediated asymmetric synthesis of beta-hydroxy ethers and its conversion to highly enantiopure beta-amino ethers.

Authors:  Kun Huang; Margarita Ortiz-Marciales; Wildeliz Correa; Edgardo Pomales; Xaira Y López
Journal:  J Org Chem       Date:  2009-06-05       Impact factor: 4.354

8.  A New and Efficient Approach to the Synthesis of Nicotine and Anabasine Analogues.

Authors:  Kun Huang; Margarita Ortiz-Marciales; Melvin De Jesús; Viatcheslav Stepanenko
Journal:  J Heterocycl Chem       Date:  2009-11-06       Impact factor: 2.193
  8 in total

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