A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä
Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers
Tekijät: Sundell R, Turcu MC, Kanerva LT
Kustantaja: BENTHAM SCIENCE PUBL LTD
Julkaisuvuosi: 2013
Journal: Current Organic Chemistry
Tietokannassa oleva lehden nimi: CURRENT ORGANIC CHEMISTRY
Lehden akronyymi: CURR ORG CHEM
Numero sarjassa: 7
Vuosikerta: 17
Numero: 7
Aloitussivu: 672
Lopetussivu: 681
Sivujen määrä: 10
ISSN: 1385-2728
DOI: https://doi.org/10.2174/1385272811317070003
Tiivistelmä
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.
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.
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