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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Lipase-Catalyzed Dynamic Combinatorial Resolution and the Synthesis of Heteroaromatic Cyanohydrin Ester Enantiomers

Author(s): Riku Sundell, Mihaela C. Turcu and Liisa T. Kanerva

Volume 17, Issue 7, 2013

Page: [672 - 681] Pages: 10

DOI: 10.2174/1385272811317070003

Price: $65


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.

Keywords: Dynamic combinatorial resolution, dynamic kinetic resolution, cyanohydrin, lipase catalysis, acylation, enzyme catalysis, base catalysis.

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