Heterogeneous Raney Nickel and Cobalt Catalysts for Racemization and Dynamic Kinetic Resolution of Amines
Raney metals were studied as heterogeneous catalysts for racemization and dynamic kinetic resolution (DKR) of chiral amines, as an alternative to metals like palladium or ruthenium. Both Raney nickel and cobalt were able to selectively racemize various chiral amines with high selectivity. In the rac...
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| Published in: | Advanced synthesis & catalysis Vol. 350; no. 1; pp. 113 - 121 |
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| Format: | Journal Article |
| Language: | English |
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Weinheim
WILEY-VCH Verlag
04.01.2008
WILEY‐VCH Verlag Wiley |
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| ISSN: | 1615-4150, 1615-4169 |
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| Abstract | Raney metals were studied as heterogeneous catalysts for racemization and dynamic kinetic resolution (DKR) of chiral amines, as an alternative to metals like palladium or ruthenium. Both Raney nickel and cobalt were able to selectively racemize various chiral amines with high selectivity. In the racemization of benzylic primary amines, the minor formation of side products, e.g., secondary amines, can be suppressed by varying the hydrogen pressure. In the racemization of aliphatic amines over Raney catalysts, the selectivity is very high, with the enantiomeric amine as the sole product. DKR of racemic aliphatic amines can be performed with immobilized Candida antarctica lipase B and Raney nickel in one pot; for 2‐hexylamine, a yield of 95 % of the acetylated amide was achieved, with 97 % ee. Attention is devoted to the compatibility of the enzyme and the metal catalyst during the DKR. For benzylic primary amines, a two‐pot process is proposed in which the liquid is alternatingly shuttled between two vessels containing the solid racemization catalyst and the biocatalyst. After 4 such cycles, the amide of (R)‐1‐phenylethylamine was obtained with 94 % yield and more than 90 % ee. |
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| AbstractList | Raney metals were studied as heterogeneous catalysts for racemization and dynamic kinetic resolution (DKR) of chiral amines, as an alternative to metals like palladium or ruthenium. Both Raney nickel and cobalt were able to selectively racemize various chiral amines with high selectivity. In the racemization of benzylic primary amines, the minor formation of side products, e.g., secondary amines, can be suppressed by varying the hydrogen pressure. In the racemization of aliphatic amines over Raney catalysts, the selectivity is very high, with the enantiomeric amine as the sole product. DKR of racemic aliphatic amines can be performed with immobilized Candida antarctica lipase B and Raney nickel in one pot; for 2-hexylamine, a yield of 95% of the acetylated amide was achieved, with 97% ee. Attention is devoted to the compatibility of the enzyme and the metal catalyst during the DKR. For benzylic primary amines, a two-pot process is proposed in which the liquid is alternatingly shuttled between two vessels containing the solid racemization catalyst and the biocatalyst. After 4 such cycles, the amide of (R)-1-phenylethylamine was obtained with 94% yield and more than 90% ee. |
| Author | Parvulescu, Andrei N. De Vos, Dirk E. Jacobs, Pierre A. |
| Author_xml | – sequence: 1 givenname: Andrei N. surname: Parvulescu fullname: Parvulescu, Andrei N. organization: Centre for Surface Chemistry and Catalysis, K.U.Leuven, Kasteelpark Arenberg 23, 3001 Leuven, Belgium, Fax: (+32)-16-32-1998 – sequence: 2 givenname: Pierre A. surname: Jacobs fullname: Jacobs, Pierre A. organization: Centre for Surface Chemistry and Catalysis, K.U.Leuven, Kasteelpark Arenberg 23, 3001 Leuven, Belgium, Fax: (+32)-16-32-1998 – sequence: 3 givenname: Dirk E. surname: De Vos fullname: De Vos, Dirk E. email: dirk.devos@biw.kuleuven.be organization: Centre for Surface Chemistry and Catalysis, K.U.Leuven, Kasteelpark Arenberg 23, 3001 Leuven, Belgium, Fax: (+32)-16-32-1998 |
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| Keywords | PALLADIUM chiral amines ACYLATION Raney nickel RUTHENIUM Raney cobalt COMBINATION resolution ASYMMETRIC TRANSFORMATIONS SECONDARY ALCOHOLS TEMPERATURE chiral amides kinetic resolution LIPASE EFFICIENT dynamic kinetic |
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| Snippet | Raney metals were studied as heterogeneous catalysts for racemization and dynamic kinetic resolution (DKR) of chiral amines, as an alternative to metals like... |
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| SubjectTerms | Chemistry Chemistry, Applied Chemistry, Organic chiral amides chiral amines dynamic kinetic resolution kinetic resolution Physical Sciences Raney cobalt Raney nickel Science & Technology |
| Title | Heterogeneous Raney Nickel and Cobalt Catalysts for Racemization and Dynamic Kinetic Resolution of Amines |
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