Literature DB >> 20401380

Omega-transaminases as efficient biocatalysts to obtain novel chiral selenium-amine ligands for Pd-catalysis.

Leandro H Andrade1, Alexandre V Silva, Priscila Milani, Dominik Koszelewski, Wolfgang Kroutil.   

Abstract

Omega-transaminases have been evaluated as biocatalysts in the reductive amination of organoselenium acetophenones to the corresponding amines, and in the kinetic resolution of racemic organoselenium amines. Kinetic resolution proved to be more efficient than the asymmetric reductive amination. By using these methodologies we were able to obtain both amine enantiomers in high enantiomeric excess (up to 99%). Derivatives of the obtained optically pure o-selenium 1-phenylethyl amine were evaluated as ligands in the palladium-catalyzed asymmetric alkylation, giving the alkylated product in up to 99% ee.

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Year:  2010        PMID: 20401380     DOI: 10.1039/b920946h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  5 in total

1.  Selenophenes: Introducing a New Element into the Core of Non-Steroidal Estrogen Receptor Ligands.

Authors:  Silong Zhang; Zhiyong Wang; Zhiye Hu; Changhao Li; Chu Tang; Kathryn E Carlson; Junjie Luo; Chune Dong; John A Katzenellenbogen; Jian Huang; Hai-Bing Zhou
Journal:  ChemMedChem       Date:  2017-01-09       Impact factor: 3.466

2.  Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts.

Authors:  Wolfgang Kroutil; Eva-Maria Fischereder; Christine S Fuchs; Horst Lechner; Francesco G Mutti; Desiree Pressnitz; Aashrita Rajagopalan; Johann H Sattler; Robert C Simon; Elina Siirola
Journal:  Org Process Res Dev       Date:  2013-04-22       Impact factor: 3.317

3.  An investigation of the observed, but counter-intuitive, stereoselectivity noted during chiral amine synthesis via N-chiral-ketimines.

Authors:  Thomas C Nugent; Richard Vaughan Williams; Andrei Dragan; Alejandro Alvarado Méndez; Andrei V Iosub
Journal:  Beilstein J Org Chem       Date:  2013-10-15       Impact factor: 2.883

4.  The Industrial Age of Biocatalytic Transamination.

Authors:  Michael Fuchs; Judith E Farnberger; Wolfgang Kroutil
Journal:  European J Org Chem       Date:  2015-09-23

5.  An Efficient Method for Selective Syntheses of Sodium Selenide and Dialkyl Selenides.

Authors:  Na Hye Shin; Yoo Jin Lim; Chorong Kim; Ye Eun Kim; Yu Ra Jeong; Hyunsung Cho; Myung-Sook Park; Sang Hyup Lee
Journal:  Molecules       Date:  2022-08-16       Impact factor: 4.927

  5 in total

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