Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B
The substrate scope in the dynamic kinetic resolution of secondary alcohols was studied by using 31 structurally different alcohols and isopropenyl acetate in the presence of dicarbonylchlorido(pentabenzylcyclopentadienyl) ruthenium and Candida antarctica lipase B (Novozym 435, CAL-B) in toluene. Th...
Published in: | European Journal of Organic Chemistry |
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ftaboakademicris:oai:pure.atira.dk:publications/913249b7-a86d-454f-8cdf-e84039734051 2023-05-15T14:00:38+02:00 Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B Paivio, M Mavrynsky, Denys Leino, Reko Kanerva, LT 2011 https://research.abo.fi/en/publications/913249b7-a86d-454f-8cdf-e84039734051 https://doi.org/10.1002/ejoc.201001703 und unknown info:eu-repo/semantics/restrictedAccess Paivio , M , Mavrynsky , D , Leino , R & Kanerva , LT 2011 , ' Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B ' , European Journal of Organic Chemistry , no. 8 , pp. 1452–1457 . https://doi.org/10.1002/ejoc.201001703 Cyclopentadienyl ligands Dynamic kinetic resolution Enantioselectivity Enzyme catalysis Racemization article 2011 ftaboakademicris https://doi.org/10.1002/ejoc.201001703 2022-12-04T14:19:39Z The substrate scope in the dynamic kinetic resolution of secondary alcohols was studied by using 31 structurally different alcohols and isopropenyl acetate in the presence of dicarbonylchlorido(pentabenzylcyclopentadienyl) ruthenium and Candida antarctica lipase B (Novozym 435, CAL-B) in toluene. The enzyme and the ruthenium complex were shown to function in a highly compatible manner allowing the conversion of the racemic alcohols into the (R)-acetates in practically theoretical yields and, in most cases, ee values exceeding 99%. The results are fully comparable to those published previously by using earlier reported, state-of-the-art ruthenium-based catalysts for the alcohol racemization. A clear benefit of the dicarbonylchlorido(pentabenzylcyclopentadienyl) ruthenium system, when compared to other (cyclopentadienyl) ruthenium racemization catalysts, is its simple and cost-efficient preparation. Article in Journal/Newspaper Antarc* Antarctica Åbo Akademi University Research Portal European Journal of Organic Chemistry 2011 8 1452 1457 |
institution |
Open Polar |
collection |
Åbo Akademi University Research Portal |
op_collection_id |
ftaboakademicris |
language |
unknown |
topic |
Cyclopentadienyl ligands Dynamic kinetic resolution Enantioselectivity Enzyme catalysis Racemization |
spellingShingle |
Cyclopentadienyl ligands Dynamic kinetic resolution Enantioselectivity Enzyme catalysis Racemization Paivio, M Mavrynsky, Denys Leino, Reko Kanerva, LT Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B |
topic_facet |
Cyclopentadienyl ligands Dynamic kinetic resolution Enantioselectivity Enzyme catalysis Racemization |
description |
The substrate scope in the dynamic kinetic resolution of secondary alcohols was studied by using 31 structurally different alcohols and isopropenyl acetate in the presence of dicarbonylchlorido(pentabenzylcyclopentadienyl) ruthenium and Candida antarctica lipase B (Novozym 435, CAL-B) in toluene. The enzyme and the ruthenium complex were shown to function in a highly compatible manner allowing the conversion of the racemic alcohols into the (R)-acetates in practically theoretical yields and, in most cases, ee values exceeding 99%. The results are fully comparable to those published previously by using earlier reported, state-of-the-art ruthenium-based catalysts for the alcohol racemization. A clear benefit of the dicarbonylchlorido(pentabenzylcyclopentadienyl) ruthenium system, when compared to other (cyclopentadienyl) ruthenium racemization catalysts, is its simple and cost-efficient preparation. |
format |
Article in Journal/Newspaper |
author |
Paivio, M Mavrynsky, Denys Leino, Reko Kanerva, LT |
author_facet |
Paivio, M Mavrynsky, Denys Leino, Reko Kanerva, LT |
author_sort |
Paivio, M |
title |
Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B |
title_short |
Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B |
title_full |
Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B |
title_fullStr |
Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B |
title_full_unstemmed |
Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B |
title_sort |
dynamic kinetic resolution of a wide range of secondary alcohols: cooperation of dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and cal-b |
publishDate |
2011 |
url |
https://research.abo.fi/en/publications/913249b7-a86d-454f-8cdf-e84039734051 https://doi.org/10.1002/ejoc.201001703 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Paivio , M , Mavrynsky , D , Leino , R & Kanerva , LT 2011 , ' Dynamic Kinetic Resolution of a Wide Range of Secondary Alcohols: Cooperation of Dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium and CAL-B ' , European Journal of Organic Chemistry , no. 8 , pp. 1452–1457 . https://doi.org/10.1002/ejoc.201001703 |
op_rights |
info:eu-repo/semantics/restrictedAccess |
op_doi |
https://doi.org/10.1002/ejoc.201001703 |
container_title |
European Journal of Organic Chemistry |
container_volume |
2011 |
container_issue |
8 |
container_start_page |
1452 |
op_container_end_page |
1457 |
_version_ |
1766269867829231616 |