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

Gajewy J, Gawronski J, Kwit M - Monatsh. Chem. (2012)

Bottom Line: Chiral acyclic and macrocyclic amines derived from 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, A. Mickiewicz University, 60-780 Poznan, Poland.

ABSTRACT

Abstract: Chiral acyclic and macrocyclic amines derived from 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.

No MeSH data available.


Acyclic and cyclic ligands used in this study
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Fig1: Acyclic and cyclic ligands used in this study

Mentions: The main objective of this work was to test several acyclic or cyclic ligands derived from enantiomerically pure trans-1,2-diaminocyclohexane, which are secondary or tertiary diamines, imines, or heteraphanes with additional substituents with potential coordinating character (Fig. 1).Fig. 1


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

Gajewy J, Gawronski J, Kwit M - Monatsh. Chem. (2012)

Acyclic and cyclic ligands used in this study
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4494764&req=5

Fig1: Acyclic and cyclic ligands used in this study
Mentions: The main objective of this work was to test several acyclic or cyclic ligands derived from enantiomerically pure trans-1,2-diaminocyclohexane, which are secondary or tertiary diamines, imines, or heteraphanes with additional substituents with potential coordinating character (Fig. 1).Fig. 1

Bottom Line: Chiral acyclic and macrocyclic amines derived from 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, A. Mickiewicz University, 60-780 Poznan, Poland.

ABSTRACT

Abstract: Chiral acyclic and macrocyclic amines derived from 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.

No MeSH data available.