Literature DB >> 19554205

Enantioselective Reduction of Prochiral Ketones using Spiroborate Esters as Catalysts.

Viatcheslav Stepanenko1, Melvin De Jesus, Wildeliz Correa, Irisbel Guzman, Cindybeth Vazquez, Wilanet de la Cruz, Margarita Ortiz-Marciales, Charles L Barnes.   

Abstract

Novel spiroborate esters derived nonracemic 1,2-aminoalcohols and ethylene glycol are reported as highly effective catalysts for the asymmetric borane reduction of a variety of prochiral ketones with borane-dimethyl sulfide complex at room temperature. Optically active alcohols were obtained in excellent chemical yields using 0.1 to 10 mol % of catalysts with up to 99% ee.

Entities:  

Year:  2007        PMID： 19554205      PMCID： PMC2701200          DOI： 10.1016/j.tetlet.2007.06.086

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  7 in total

1.  Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis.

Authors:  F Fache; E Schulz; M L Tommasino; M Lemaire
Journal:  Chem Rev       Date:  2000-06-14       Impact factor: 60.622

2.  (S)-selective kinetic resolution and chemoenzymatic dynamic kinetic resolution of secondary alcohols.

Authors:  Linnéa Borén; Belén Martín-Matute; Yongmei Xu; Armando Córdova; Jan-E Bäckvall
Journal:  Chemistry       Date:  2005-12-16       Impact factor: 5.236

3.  Enantioselective enzymatic reductions of sterically bulky aryl alkyl ketones catalyzed by a NADPH-dependent carbonyl reductase.

Authors:  Dunming Zhu; Ling Hua
Journal:  J Org Chem       Date:  2006-12-08       Impact factor: 4.354

Review 4.  Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

5.  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

6.  Stereoselective ketone reduction by a carbonyl reductase from Sporobolomyces salmonicolor. Substrate specificity, enantioselectivity and enzyme-substrate docking studies.

Authors:  Dunming Zhu; Yan Yang; John D Buynak; Ling Hua
Journal:  Org Biomol Chem       Date:  2006-06-15       Impact factor: 3.876

7.  Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis.

Authors:  Ingo Schiffers; Toni Rantanen; Frank Schmidt; Werner Bergmans; Lorenzo Zani; Carsten Bolm
Journal:  J Org Chem       Date:  2006-03-17       Impact factor: 4.354
  7 in total
  6 in total

1.  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

2.  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

3.  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

4.  Novel dimethoxy(aminoalkoxy)borate derived from (S)-diphenylprolinol as highly efficient catalyst for the enantioselective boron-mediated reduction of prochiral ketones.

Authors:  Viatcheslav Stepanenko; Margarita Ortiz-Marciales; Charles L Barnes; Carmelo Garcia
Journal:  Tetrahedron Lett       Date:  2009-03-04       Impact factor: 2.415

5.  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

Review 6.  Practical Enantioselective Reduction of Ketones Using Oxazaborolidine Catalysts Generated In Situ from Chiral Lactam Alcohols.

Authors:  Yasuhiro Kawanami; Ryo C Yanagita
Journal:  Molecules       Date:  2018-09-20       Impact factor: 4.411
  6 in total

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