Convenient, enantioselective hydrosilylation of imines in protic media catalyzed by a Zn-trianglamine complex
Chiral hexamine macrocycle derived from trans-1,2-diaminocyclohexane (DACH) in a complex with diethylzinc efficiently catalyzes the asymmetric hydrosilylation of N-phosphorylated aryl-alkyl or aryl-aryl ketimines in protic media with enantiomeric excess of the product approaching 100%. The cyclic st...
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| Published in | Organic & biomolecular chemistry Vol. 9; no. 10; pp. 3863 - 3870 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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CAMBRIDGE
Royal Soc Chemistry
21.05.2011
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| Online Access | Get full text |
| ISSN | 1477-0520 1477-0539 1477-0539 |
| DOI | 10.1039/c1ob05074e |
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| Abstract | Chiral hexamine macrocycle derived from trans-1,2-diaminocyclohexane (DACH) in a complex with diethylzinc efficiently catalyzes the asymmetric hydrosilylation of N-phosphorylated aryl-alkyl or aryl-aryl ketimines in protic media with enantiomeric excess of the product approaching 100%. The cyclic structure of the trianglamine ligand increases the enantioselectivity and/or the yield of the reaction, in comparison to the catalysis by acyclic N,N'-dibenzyl-DACH ligands. Density functional theory (DFT) computations on the structure of the model ligand-zinc complex and on the structures of the pre-organized reactants together with the calculations of possible transition states allow rationalization of the direction of the asymmetric induction of the hydrosilylation reaction. This is the first example of asymmetric catalysis of the hydrosilylation reaction of ketimines with the use of a readily available and inexpensive macrocyclic trianglamine ligand. |
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| AbstractList | Chiral hexamine macrocycle derived from trans-1,2-diaminocyclohexane (DACH) in a complex with diethylzinc efficiently catalyzes the asymmetric hydrosilylation of N-phosphorylated aryl-alkyl or aryl-aryl ketimines in protic media with enantiomeric excess of the product approaching 100%. The cyclic structure of the trianglamine ligand increases the enantioselectivity and/or the yield of the reaction, in comparison to the catalysis by acyclic N,N'-dibenzyl-DACH ligands. Density functional theory (DFT) computations on the structure of the model ligand-zinc complex and on the structures of the pre-organized reactants together with the calculations of possible transition states allow rationalization of the direction of the asymmetric induction of the hydrosilylation reaction. This is the first example of asymmetric catalysis of the hydrosilylation reaction of ketimines with the use of a readily available and inexpensive macrocyclic trianglamine ligand. Chiral hexamine macrocycle derived from trans-1,2-diaminocyclohexane (DACH) in a complex with diethylzinc efficiently catalyzes the asymmetric hydrosilylation of N-phosphorylated aryl-alkyl or aryl-aryl ketimines in protic media with enantiomeric excess of the product approaching 100%. The cyclic structure of the trianglamine ligand increases the enantioselectivity and/or the yield of the reaction, in comparison to the catalysis by acyclic N,N'-dibenzyl-DACH ligands. Density functional theory (DFT) computations on the structure of the model ligand-zinc complex and on the structures of the pre-organized reactants together with the calculations of possible transition states allow rationalization of the direction of the asymmetric induction of the hydrosilylation reaction. This is the first example of asymmetric catalysis of the hydrosilylation reaction of ketimines with the use of a readily available and inexpensive macrocyclic trianglamine ligand.Chiral hexamine macrocycle derived from trans-1,2-diaminocyclohexane (DACH) in a complex with diethylzinc efficiently catalyzes the asymmetric hydrosilylation of N-phosphorylated aryl-alkyl or aryl-aryl ketimines in protic media with enantiomeric excess of the product approaching 100%. The cyclic structure of the trianglamine ligand increases the enantioselectivity and/or the yield of the reaction, in comparison to the catalysis by acyclic N,N'-dibenzyl-DACH ligands. Density functional theory (DFT) computations on the structure of the model ligand-zinc complex and on the structures of the pre-organized reactants together with the calculations of possible transition states allow rationalization of the direction of the asymmetric induction of the hydrosilylation reaction. This is the first example of asymmetric catalysis of the hydrosilylation reaction of ketimines with the use of a readily available and inexpensive macrocyclic trianglamine ligand. |
| Author | Kwit, Marcin Gawronski, Jacek Gajewy, Jadwiga |
| Author_xml | – sequence: 1 givenname: Jadwiga surname: Gajewy fullname: Gajewy, Jadwiga – sequence: 2 givenname: Jacek surname: Gawronski fullname: Gawronski, Jacek – sequence: 3 givenname: Marcin surname: Kwit fullname: Kwit, Marcin |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/21445430$$D View this record in MEDLINE/PubMed |
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| Keywords | ASYMMETRIC HYDROSILYLATION KETONES REDUCTION POLYMETHYLHYDROSILOXANE |
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| Snippet | Chiral hexamine macrocycle derived from trans-1,2-diaminocyclohexane (DACH) in a complex with diethylzinc efficiently catalyzes the asymmetric hydrosilylation... |
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| SubjectTerms | Catalysis Chemistry Chemistry, Organic Imines - chemistry Macrocyclic Compounds - chemistry Models, Molecular Molecular Conformation Organometallic Compounds - chemistry Physical Sciences Quantum Theory Science & Technology Silicon - chemistry Solvents - chemistry Stereoisomerism Substrate Specificity Zinc - chemistry |
| Title | Convenient, enantioselective hydrosilylation of imines in protic media catalyzed by a Zn-trianglamine complex |
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