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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.


Diols and alcohols used as activators in [Zn(diamine)(diol)]-catalyzed hydrosilylations
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Fig2: Diols and alcohols used as activators in [Zn(diamine)(diol)]-catalyzed hydrosilylations

Mentions: We tested several diols (Fig. 2), either chiral or achiral, in combination with appropriate diamines. For chiral diols both enantiomers and racemic mixtures were used, if available.Fig. 2


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

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

Diols and alcohols used as activators in [Zn(diamine)(diol)]-catalyzed hydrosilylations
© Copyright Policy
Related In: Results  -  Collection

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

Fig2: Diols and alcohols used as activators in [Zn(diamine)(diol)]-catalyzed hydrosilylations
Mentions: We tested several diols (Fig. 2), either chiral or achiral, in combination with appropriate diamines. For chiral diols both enantiomers and racemic mixtures were used, if available.Fig. 2

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.