Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol
An improved gram-scale synthesis of Bn5CpRu(CO)(2)Cl is reported based on heating of pentabenzylcyclopentadiene with Ru-3(CO)(12) at 160 degrees C under argon atmosphere in mesitylene followed by addition of chloroform, continued heating, and evaporation of the solvents. Subsequent washing of unreac...
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ftaboakademicris:oai:pure.atira.dk:publications/0cdeb2e9-29c0-4d61-beb3-3f95ce502d5b 2023-05-15T14:00:38+02:00 Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol Mavrynsky, Denys Kanerva, LT Sillanpaa, R Leino, Reko 2011 https://research.abo.fi/en/publications/0cdeb2e9-29c0-4d61-beb3-3f95ce502d5b https://doi.org/10.1351/PAC-CON-10-09-05 und unknown info:eu-repo/semantics/restrictedAccess Mavrynsky , D , Kanerva , LT , Sillanpaa , R & Leino , R 2011 , ' Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol ' , Pure and Applied Chemistry , vol. 83 , no. 3 , pp. 479–487 . https://doi.org/10.1351/PAC-CON-10-09-05 chemoenzymatic synthesis cyclopentadienyl dynamic kinetic resolution (DKR) Novozym ruthenium article 2011 ftaboakademicris https://doi.org/10.1351/PAC-CON-10-09-05 2022-12-04T14:20:41Z An improved gram-scale synthesis of Bn5CpRu(CO)(2)Cl is reported based on heating of pentabenzylcyclopentadiene with Ru-3(CO)(12) at 160 degrees C under argon atmosphere in mesitylene followed by addition of chloroform, continued heating, and evaporation of the solvents. Subsequent washing of unreacted ligand precursor with hexane provided pure title compound in 77 % yield. In combination with Candida antarctica lipase B (CAL-B) (Novozym 435), this complex forms a highly active racemization catalyst for metallo enzymatic dynamic kinetic resolution (DKR) of secondary alcohols as demonstrated in the present work by converting 100 g of racemic 1-phenylethanol to (R)-1-phenylethanol in > 99 % ee and 93 % overall yield over two steps using 0.05 mol % loading of the metal catalyst and 1 mass % loading of immobilized enzyme. In addition, the synthesis and crystallographic characterization of the palladium congener Bn5CpPd(PPh3)Cl are briefly discussed. Article in Journal/Newspaper Antarc* Antarctica Åbo Akademi University Research Portal Pure and Applied Chemistry 83 3 479 487 |
institution |
Open Polar |
collection |
Åbo Akademi University Research Portal |
op_collection_id |
ftaboakademicris |
language |
unknown |
topic |
chemoenzymatic synthesis cyclopentadienyl dynamic kinetic resolution (DKR) Novozym ruthenium |
spellingShingle |
chemoenzymatic synthesis cyclopentadienyl dynamic kinetic resolution (DKR) Novozym ruthenium Mavrynsky, Denys Kanerva, LT Sillanpaa, R Leino, Reko Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
topic_facet |
chemoenzymatic synthesis cyclopentadienyl dynamic kinetic resolution (DKR) Novozym ruthenium |
description |
An improved gram-scale synthesis of Bn5CpRu(CO)(2)Cl is reported based on heating of pentabenzylcyclopentadiene with Ru-3(CO)(12) at 160 degrees C under argon atmosphere in mesitylene followed by addition of chloroform, continued heating, and evaporation of the solvents. Subsequent washing of unreacted ligand precursor with hexane provided pure title compound in 77 % yield. In combination with Candida antarctica lipase B (CAL-B) (Novozym 435), this complex forms a highly active racemization catalyst for metallo enzymatic dynamic kinetic resolution (DKR) of secondary alcohols as demonstrated in the present work by converting 100 g of racemic 1-phenylethanol to (R)-1-phenylethanol in > 99 % ee and 93 % overall yield over two steps using 0.05 mol % loading of the metal catalyst and 1 mass % loading of immobilized enzyme. In addition, the synthesis and crystallographic characterization of the palladium congener Bn5CpPd(PPh3)Cl are briefly discussed. |
format |
Article in Journal/Newspaper |
author |
Mavrynsky, Denys Kanerva, LT Sillanpaa, R Leino, Reko |
author_facet |
Mavrynsky, Denys Kanerva, LT Sillanpaa, R Leino, Reko |
author_sort |
Mavrynsky, Denys |
title |
Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_short |
Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_full |
Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_fullStr |
Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_full_unstemmed |
Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_sort |
improved synthesis of bn5cpru(co)(2)cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
publishDate |
2011 |
url |
https://research.abo.fi/en/publications/0cdeb2e9-29c0-4d61-beb3-3f95ce502d5b https://doi.org/10.1351/PAC-CON-10-09-05 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Mavrynsky , D , Kanerva , LT , Sillanpaa , R & Leino , R 2011 , ' Improved synthesis of Bn5CpRu(CO)(2)Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol ' , Pure and Applied Chemistry , vol. 83 , no. 3 , pp. 479–487 . https://doi.org/10.1351/PAC-CON-10-09-05 |
op_rights |
info:eu-repo/semantics/restrictedAccess |
op_doi |
https://doi.org/10.1351/PAC-CON-10-09-05 |
container_title |
Pure and Applied Chemistry |
container_volume |
83 |
container_issue |
3 |
container_start_page |
479 |
op_container_end_page |
487 |
_version_ |
1766269867995955200 |