Literature DB >> 26166868

Asymmetric hydrosilylation of ketones catalyzed by complexes formed from trans-diaminocyclohexane-based diamines and diethylzinc.

Jadwiga Gajewy1, Jacek Gawronski1, Marcin Kwit1.   

Abstract

ABSTRACT: Chiral acyclic and macrocyclic amines derived from n class="Chemical">trans-1,2-diaminocyclohexane in complexes with diethylzinc efficiently catalyze asymmetric hydrosilylation of aryl-alkyl and aryl-aryl ketones with enantiomeric excess of the product up to 86 %. A trianglamine ligand with a cyclic structure or the presence of an additional coordinating group increases the enantioselectivity of the reaction, in comparison with catalysis by a simple acyclic N,N'-dibenzyl-1,2-diaminocyclohexane ligand. In addition, the effect of the asymmetric activation of the catalyst by a variety of alcohols and diols is studied.

Entities:  

Keywords:  Asymmetric activation; Homogeneous catalysis; Ligands; Macrocycles; Metal complexes; Zinc

Year:  2012        PMID: 26166868      PMCID: PMC4494764          DOI: 10.1007/s00706-012-0754-0

Source DB:  PubMed          Journal:  Monatsh Chem        ISSN: 0026-9247            Impact factor:   1.451


  29 in total

1.  Convenient, enantioselective hydrosilylation of imines in protic media catalyzed by a Zn-trianglamine complex.

Authors:  Jadwiga Gajewy; Jacek Gawronski; Marcin Kwit
Journal:  Org Biomol Chem       Date:  2011-03-29       Impact factor: 3.876

2.  Synthesis, structure, and contrasting chiroptical properties of large trianglimine macrocycles.

Authors:  Marcin Kwit; Paweł Skowronek; Halina Kołbon; Jacek Gawroński
Journal:  Chirality       Date:  2005       Impact factor: 2.437

3.  Enantioselective rhodium-catalyzed addition of arylboronic acids to aldehydes using chiral spiro monophosphite ligands.

Authors:  Hai-Feng Duan; Jian-Hua Xie; Wen-Jian Shi; Qi Zhang; Qi-Lin Zhou
Journal:  Org Lett       Date:  2006-03-30       Impact factor: 6.005

Review 4.  Chiral monodentate phosphine ligand MOP for transition-metal-catalyzed asymmetric reactions.

Authors:  T Hayashi
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

5.  Efficient syntheses of fluorinated aryl alcohols of high enantiomeric purity via boronic esters

Authors: 
Journal:  J Org Chem       Date:  2000-11-17       Impact factor: 4.354

6.  Trianglamines--readily prepared, conformationally flexible inclusion-forming chiral hexamines.

Authors:  Jacek Gawronski; Krystyna Gawronska; Jakub Grajewski; Marcin Kwit; Agnieszka Plutecka; Urszula Rychlewska
Journal:  Chemistry       Date:  2006-02-08       Impact factor: 5.236

7.  Controlling the macrocycle size by the stoichiometry of the applied template ion.

Authors:  Aleksandra Sarnicka; Przemysław Starynowicz; Jerzy Lisowski
Journal:  Chem Commun (Camb)       Date:  2012-01-18       Impact factor: 6.222

8.  Direct Zn-diamine promoted reduction of C=O and C=N bonds by polymethylhydrosiloxane in methanol.

Authors:  Virginie Bette; André Mortreux; Christian W Lehmann; Jean-François Carpentier
Journal:  Chem Commun (Camb)       Date:  2003-02-07       Impact factor: 6.222

9.  Copper, silver, and gold complexes in hydrosilylation reactions.

Authors:  Silvia Díez-González; Steven P Nolan
Journal:  Acc Chem Res       Date:  2008-02       Impact factor: 22.384

10.  Optimization of catalyst enantioselectivity and activity using achiral and meso ligands.

Authors:  Anna M Costa; Ciril Jimeno; Jason Gavenonis; Patrick J Carroll; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419

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