Practical access to (S)- heterocyclic aromatic acetates via CAL-B /Na 2 CO 3 -deacylation and Mitsunobu reaction protocol

• Main Authors: Louisa Aribi-Zouioueche (560409), Mounia Merabet-Khelassi (560408), Nabila Braïa (12023743), Martial Toffano (3164895)
• Format: Other Non-Article Part of Journal/Newspaper
• Language: unknown
• Published: 2022
• Subjects: Biophysics; Biochemistry; Microbiology; Molecular Biology; Pharmacology; Biotechnology; Ecology; Sociology; Infectious Diseases; Plant Biology; Chemical Sciences not elsewhere classified; Heteroaromatic carbinol; enzymatic kinetic resolution; hydrolysis; CAL-B; Na2CO3; deracemization; Antarc*; Antarctica
• Online Access: https://doi.org/10.6084/m9.figshare.19096582.v1

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 /Na 2 CO 3 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.