85828-09-7Relevant articles and documents
Practical access to (S)-heterocyclic aromatic acetates via CAL-B/Na2CO3-deacylation and Mitsunobu reaction protocol
Aribi-Zouioueche, Louisa,Bra?a, Nabila,Merabet-Khelassi, Mounia,Toffano, Martial
, (2022/02/11)
Herein, we report the preparation of enantiomerically pure forms of 2,3-dihydrobenzofuran-3-ol (1), chroman-4-ol (2), thiochroman-4-ol (3), 1-(furan-2-yl) ethanol (5) and 1-(thiophen-2-yl) ethanol (6), through a kinetic resolution catalysed by Candida antarctica lipase B/Na2CO3 hydrolysis sequence in organic media. The (R)-furnished alcohols and the (S)-remained acetates are recovered enantiopures (ee?>99%, E???200, Conv = 50%). Those ideal enzymatic kinetic resolution (EKRs) are well incorporated to the Mitsunobu inversion protocol in a one pot procedure to give (S)-heterocyclic acetates (1a–3a) in good to high enantiomeric excess (88%–92% ee). Whilst, the (S)-heteroaromatic acetates (5a and 6a) are given with moderate enantiomeric excess (51%–62% ee). All the (S)-acetates are given in good isolated chemical yields (>80%) allowing to overcome the maximum of 50% yield which could be usually reached in a regular kinetic resolution processes.
Lipase-catalysed kinetic resolutions of secondary alcohols in pressurised liquid hydrofluorocarbons
Ball, Anthony J.,Corr, Stuart,Micklefield, Jason
supporting information; experimental part, p. 3543 - 3546 (2009/10/26)
Three model secondary alcohols have been subjected to enzymatic kinetic resolution using three common lipases and a typical acyl donor. The resolutions were performed in two pressurised low-boiling hydrofluorocarbons, which are novel media for enzymatic reactions, and five conventional organic solvents. In general, higher yields, ee's and rates of reaction were observed in the hydrofluorocarbons.
A divergent synthesis of uncommon sugars from furanaldehyde
Zhu, Lizhi,Talukdar, Arindam,Zhang, Guisheng,Kedenburg, James P.,Wang, Peng George
, p. 1547 - 1550 (2007/10/03)
A practical synthetic strategy has been developed for producing uncommon sugars. This method employed kinetic enzymatic resolution of 1-(2-furyl)ethanol, and followed by NBS-mediated Achmatowicz rearrangement to construct α,β-unsaturated lactones. After further derivatization, five representative uncommon sugar units were successfully synthesized. Georg Thieme Verlag Stuttgart.