Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers
Five structurally related thiophene-based aldehydes, acetone cyanohydrin, a base, a lipase enzyme and isopropenyl acetate have been mixed in one-pot, leading to the dynamic combinatorial resolution of a cyanohydrin library. The process is applied in optimizing synthetic conditions for the cyanohydri...
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BENTHAM SCIENCE PUBL LTD
2022
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ftunivturku:oai:www.utupub.fi:10024/170650 2023-05-15T13:35:30+02:00 Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers Sundell R Kanerva LT Turcu MC PÄÄT Farmakologia lääkekehitys ja lääkehoito, PÄÄT Farmakologia lääkekehitys ja lääkehoito 2607102 2022-10-28T14:19:01Z 672 681 https://www.utupub.fi/handle/10024/170650 en eng BENTHAM SCIENCE PUBL LTD Alankomaat Netherlands NL 17 10.2174/1385272811317070003 Current Organic Chemistry 7 https://www.utupub.fi/handle/10024/170650 URN:NBN:fi-fe2021042714264 1385-2728 2022 ftunivturku 2022-11-03T00:02:30Z Five structurally related thiophene-based aldehydes, acetone cyanohydrin, a base, a lipase enzyme and isopropenyl acetate have been mixed in one-pot, leading to the dynamic combinatorial resolution of a cyanohydrin library. The process is applied in optimizing synthetic conditions for the cyanohydrin acetate library obtained in terms of reactivity and enantiopurity. Anhydrous Na2CO3 and lipase PS-D (Burkholderia cepacia lipase) or Novozym 435 (Candida antarctica lipase B) preparations are shown to be the best catalyst combinations for the DCR of the substrate series in toluene. The justification of the optimized process is confirmed by preparing the thiophene -based (R)-cyanohydrin acetates with 68-99% isolated yields and 82-91 % ee using the traditional dynamic kinetic resolution of each substrate. Other/Unknown Material Antarc* Antarctica University of Turku: UTUPub |
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Open Polar |
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University of Turku: UTUPub |
op_collection_id |
ftunivturku |
language |
English |
description |
Five structurally related thiophene-based aldehydes, acetone cyanohydrin, a base, a lipase enzyme and isopropenyl acetate have been mixed in one-pot, leading to the dynamic combinatorial resolution of a cyanohydrin library. The process is applied in optimizing synthetic conditions for the cyanohydrin acetate library obtained in terms of reactivity and enantiopurity. Anhydrous Na2CO3 and lipase PS-D (Burkholderia cepacia lipase) or Novozym 435 (Candida antarctica lipase B) preparations are shown to be the best catalyst combinations for the DCR of the substrate series in toluene. The justification of the optimized process is confirmed by preparing the thiophene -based (R)-cyanohydrin acetates with 68-99% isolated yields and 82-91 % ee using the traditional dynamic kinetic resolution of each substrate. |
author2 |
PÄÄT Farmakologia lääkekehitys ja lääkehoito, PÄÄT Farmakologia lääkekehitys ja lääkehoito 2607102 |
author |
Sundell R Kanerva LT Turcu MC |
spellingShingle |
Sundell R Kanerva LT Turcu MC Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers |
author_facet |
Sundell R Kanerva LT Turcu MC |
author_sort |
Sundell R |
title |
Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers |
title_short |
Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers |
title_full |
Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers |
title_fullStr |
Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers |
title_full_unstemmed |
Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers |
title_sort |
lipase-catalyzed dynamic combinatorial resolution and the synthesis of heteroaromatic cyanohydrin ester enantiomers |
publisher |
BENTHAM SCIENCE PUBL LTD |
publishDate |
2022 |
url |
https://www.utupub.fi/handle/10024/170650 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
17 10.2174/1385272811317070003 Current Organic Chemistry 7 https://www.utupub.fi/handle/10024/170650 URN:NBN:fi-fe2021042714264 1385-2728 |
_version_ |
1766066246129811456 |