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

• Main Authors: Aribi-Zouioueche, Louisa, Merabet-Khelassi, Mounia, Braïa, Nabila, Toffano, Martial
• Format: Text
• Language: unknown
• Published: Taylor & Francis 2022
• Subjects: Biophysics; Biochemistry; Microbiology; FOS Biological sciences; Molecular Biology; Pharmacology; Biotechnology; 39999 Chemical Sciences not elsewhere classified; FOS Chemical sciences; Ecology; Sociology; FOS Sociology; 110309 Infectious Diseases; FOS Health sciences; Plant Biology; Antarc*; Antarctica
• Online Access: https://dx.doi.org/10.6084/m9.figshare.19096582.v1; https://tandf.figshare.com/articles/journal_contribution/Practical_access_to_i_S_-_i_heterocyclic_aromatic_acetates_i_via_CAL-B_i_Na_sub_2_sub_CO_sub_3_sub_-deacylation_and_Mitsunobu_reaction_protocol/19096582/1

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.