Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol
An improved gram-scale synthesis of Bn 5 CpRu(CO) 2 Cl is reported based on heating of pentabenzylcyclopentadiene with Ru 3 (CO) 12 at 160 °C under argon atmosphere in mesitylene followed by addition of chloroform, continued heating, and evaporation of the solvents. Subsequent washing of unreacted l...
Published in: | Pure and Applied Chemistry |
---|---|
Main Authors: | , , , |
Format: | Article in Journal/Newspaper |
Language: | unknown |
Published: |
Walter de Gruyter GmbH
2010
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1351/pac-con-10-09-05 https://www.degruyter.com/view/journals/pac/83/3/article-p479.xml https://www.degruyter.com/downloadpdf/journals/pac/83/3/article-p479.xml |
id |
crdegruyter:10.1351/pac-con-10-09-05 |
---|---|
record_format |
openpolar |
spelling |
crdegruyter:10.1351/pac-con-10-09-05 2023-05-15T14:11:17+02:00 Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol Mavrynsky, Denys Kanerva, Liisa T. Sillanpää, Reijo Leino, Reko 2010 http://dx.doi.org/10.1351/pac-con-10-09-05 https://www.degruyter.com/view/journals/pac/83/3/article-p479.xml https://www.degruyter.com/downloadpdf/journals/pac/83/3/article-p479.xml unknown Walter de Gruyter GmbH Pure and Applied Chemistry volume 83, issue 3, page 479-487 ISSN 1365-3075 0033-4545 General Chemical Engineering General Chemistry journal-article 2010 crdegruyter https://doi.org/10.1351/pac-con-10-09-05 2022-04-14T05:02:44Z An improved gram-scale synthesis of Bn 5 CpRu(CO) 2 Cl is reported based on heating of pentabenzylcyclopentadiene with Ru 3 (CO) 12 at 160 °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 Bn 5 CpPd(PPh 3 )Cl are briefly discussed. Article in Journal/Newspaper Antarc* Antarctica De Gruyter (via Crossref) Pure and Applied Chemistry 83 3 479 487 |
institution |
Open Polar |
collection |
De Gruyter (via Crossref) |
op_collection_id |
crdegruyter |
language |
unknown |
topic |
General Chemical Engineering General Chemistry |
spellingShingle |
General Chemical Engineering General Chemistry Mavrynsky, Denys Kanerva, Liisa T. Sillanpää, Reijo Leino, Reko Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
topic_facet |
General Chemical Engineering General Chemistry |
description |
An improved gram-scale synthesis of Bn 5 CpRu(CO) 2 Cl is reported based on heating of pentabenzylcyclopentadiene with Ru 3 (CO) 12 at 160 °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 Bn 5 CpPd(PPh 3 )Cl are briefly discussed. |
format |
Article in Journal/Newspaper |
author |
Mavrynsky, Denys Kanerva, Liisa T. Sillanpää, Reijo Leino, Reko |
author_facet |
Mavrynsky, Denys Kanerva, Liisa T. Sillanpää, Reijo Leino, Reko |
author_sort |
Mavrynsky, Denys |
title |
Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_short |
Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_full |
Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_fullStr |
Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_full_unstemmed |
Improved synthesis of Bn5CpRu(CO)2Cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
title_sort |
improved synthesis of bn5cpru(co)2cl and its application as racemization catalyst in preparative-scale metalloenzymatic dynamic kinetic resolution of 1-phenylethanol |
publisher |
Walter de Gruyter GmbH |
publishDate |
2010 |
url |
http://dx.doi.org/10.1351/pac-con-10-09-05 https://www.degruyter.com/view/journals/pac/83/3/article-p479.xml https://www.degruyter.com/downloadpdf/journals/pac/83/3/article-p479.xml |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Pure and Applied Chemistry volume 83, issue 3, page 479-487 ISSN 1365-3075 0033-4545 |
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_ |
1766283421560078336 |