Enantioselective Enzymatic Synthesis of (R)-Phenyl Alkyl Esters and Their Analogue Amides using Fatty Acids as Green Acyl Donors.
(2021) ChemistrySelect — Vol. 6, n° 48, p. 13941-13946 (2021)
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- Authors
Merabet‐Khelassi, Mounia 
Lakoud, Samia Guezane Aribi‐Zouioueche, Louisa
- Abstract
- An efficient enantioselective synthesis of a set of (R)-phenylalkylesters and their analogues amides via enzymatic acylation of 1-phenylethanol (rac-1) and 1-phenylethanamine (rac-2) using carboxylic acids with different chain-lengths as green acyl donor is reported. Three lipases are used: Candida antarctica B immobilized on acrylic resin (CAL-B) and two free lipases: Pseudomonas cepacia (PCL) and Candida rugosa (CRL). The CAL-B shows an excellent selectivity during the acylation of rac-1 without restriction due to the acyl carbon chain-length, the (R)- esters (1 a–1 f) were obtained enantiopures (ee up to 99 %). For the first time, the PCL catalyzed O-acylation allows smoothly to (R)-(1 d–1 f) with high selectivity (E⋙200) is described. The conversions increase with the length of the carbon-chain of the acyl donor (28.7 %≤C≤40 %). The CRL shows less selective and provided the (R) (1 b–1 e) with 77 %≤eep≤86.4 %. Due to its high thermostability, the CAL-B is used for the N-acylation of rac-2 and provides access to enantioenriched (R)-fatty amides (2 d–2 f) (60.7 %≤eep≤74.4 %) and the remained (S)-2 with ees>91 %.
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Citations
Benamara, N. E., Merabet‐Khelassi, M., Lakoud, S. G., Aribi‐Zouioueche, L., & Riant, O. (2021). Enantioselective Enzymatic Synthesis of (R)-Phenyl Alkyl Esters and Their Analogue Amides using Fatty Acids as Green Acyl Donors. ChemistrySelect, 6(48), 13941-13946. https://doi.org/10.1002/slct.202103831 (Original work published 2021)