Literature DB >> 20160845

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

Viatcheslav Stepanenko1, Margarita Ortiz-Marciales, Charles L Barnes, Carmelo Garcia.   

Abstract

The novel dimethoxyl(aminoalkoxy)borate 1 was isolated as a white crystalline dimer joined by H-bonding as evidenced by X-ray analysis, and demonstrated to be a highly effective catalyst for the asymmetric reduction of representative prochiral ketones with borane-DMS. Optically pure alcohols were obtained using only 1 mol% of catalyst 1 in up to 99% ee.

Entities:  

Year:  2009        PMID： 20160845      PMCID： PMC2654321          DOI： 10.1016/j.tetlet.2008.12.061

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


  4 in total

1.  Enantioselective beta-lactone formation from ketene and aldehydes catalyzed by a chiral oxazaborolidine.

Authors:  Vijay Gnanadesikan; E J Corey
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

2.  Effect of temperature on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric reduction of ketones. Noncatalytic borane reduction, a nonneglectable factor in the reduction system.

Authors:  Jiaxi Xu; Tiezheng Wei; Qihan Zhang
Journal:  J Org Chem       Date:  2003-12-26       Impact factor: 4.354

3.  Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones.

Authors:  Jiaxi Xu; Tiezheng Wei; Qihan Zhang
Journal:  J Org Chem       Date:  2004-10-01       Impact factor: 4.354

4.  Enantioselective Reduction of Prochiral Ketones using Spiroborate Esters as Catalysts.

Authors:  Viatcheslav Stepanenko; Melvin De Jesus; Wildeliz Correa; Irisbel Guzman; Cindybeth Vazquez; Wilanet de la Cruz; Margarita Ortiz-Marciales; Charles L Barnes
Journal:  Tetrahedron Lett       Date:  2007-08-13       Impact factor: 2.415
  4 in total
  4 in total

1.  Synthesis and stability of new spiroaminoborate esters.

Authors:  Viatcheslav Stepanenko; Melvin de Jesús; Carmelo Garcia; Charles L Barnes; Margarita Ortiz-Marciales
Journal:  Tetrahedron Lett       Date:  2012-02-22       Impact factor: 2.415

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.  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

4.  Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.

Authors:  Hai-Yang Wang; Kun Huang; Melvin De Jesús; Sandraliz Espinosa; Luis E Piñero-Santiago; Charles L Barnes; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2016-02-15
  4 in total

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