Literature DB >> 17397177

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

Xiaogen Huang1, Margarita Ortiz-Marciales, Kun Huang, Viatcheslav Stepanenko, Francisco G Merced, Angel M Ayala, Wildeliz Correa, Melvin De Jesús.   

Abstract

[reaction: see text] The enantioselective borane reduction of O-benzyloxime ethers to primary amines was studied under catalytic conditions using the spiroborate esters 5-10 derived from nonracemic 1,2-amino alcohols and ethylene glycol. Effective catalytic conditions were achieved using only 10% of catalyst 5 derived from diphenylvalinol in dioxane at 0 degrees C resulting in complete conversion to the corresponding primary amine in up to 99% ee.

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Year:  2007        PMID： 17397177      PMCID： PMC2571073          DOI： 10.1021/ol0704791

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Enantioselective reduction of oxime ethers with borane catalyzed by polymer-supported 2-piperazinemethanol

Authors: 
Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

2.  Enantioselective nitrile anion cyclization to substituted pyrrolidines. A highly efficient synthesis of (3S,4R)-N-tert-butyl-4-arylpyrrolidine-3-carboxylic acid.

Authors:  John Y L Chung; Raymond Cvetovich; Joseph Amato; J Christopher McWilliams; Robert Reamer; Lisa DiMichele
Journal:  J Org Chem       Date:  2005-04-29       Impact factor: 4.354

3.  Asymmetric reduction of oxime ethers promoted by chiral spiroborate esters with an O3BN framework.

Authors:  Yunbo Chu; Zixing Shan; Dejun Liu; Nannan Sun
Journal:  J Org Chem       Date:  2006-05-12       Impact factor: 4.354
  3 in total
  9 in total

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

Authors:  Viatcheslav Stepanenko; Melvin De Jesús; Wildeliz Correa; Irisbel Guzmán; Cindybeth Vázquez; Lymaris Ortiz; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2007-11-26

2.  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

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.  Nickel-catalysed asymmetric hydrogenation of oximes.

Authors:  Bowen Li; Jianzhong Chen; Dan Liu; Ilya D Gridnev; Wanbin Zhang
Journal:  Nat Chem       Date:  2022-06-13       Impact factor: 24.274

5.  A facile circular dichroism protocol for rapid determination of enantiomeric excess and concentration of chiral primary amines.

Authors:  Sonia Nieto; Justin M Dragna; Eric V Anslyn
Journal:  Chemistry       Date:  2010-01-04       Impact factor: 5.236

6.  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

7.  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

8.  Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.

Authors:  Wenhua Ou; Sandraliz Espinosa; Héctor J Meléndez; Silvia M Farré; Jaime L Alvarez; Valerie Torres; Ileanne Martínez; Kiara M Santiago; Margarita Ortiz-Marciales
Journal:  J Org Chem       Date:  2013-05-13       Impact factor: 4.354

9.  Simple ruthenium-catalyzed reductive amination enables the synthesis of a broad range of primary amines.

Authors:  Thirusangumurugan Senthamarai; Kathiravan Murugesan; Jacob Schneidewind; Narayana V Kalevaru; Wolfgang Baumann; Helfried Neumann; Paul C J Kamer; Matthias Beller; Rajenahally V Jagadeesh
Journal:  Nat Commun       Date:  2018-10-08       Impact factor: 14.919
  9 in total

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