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Chemoenzymatic synthesis of both enantiomers of 3-hydroxy-2,3-dihydro-4H-chromen-4-one

✍ Scribed by Ayhan S. Demir; Asuman Aybey; Özge Sesenoglu; Fatos Polat

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
135 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

4-Oxo-3,4-dihydro-2-chromen-3-yl acetate is synthesized using manganese(III)acetate starting from 2,3-dihydro-4Hchromen-4-one. K 2 CO 3 mediated hydrolysis of 4-oxo-3,4-dihdro-2-chromen-3-yl acetate furnished 3-hydroxy-2,3-dihydro-4Hchromen-4-one in high yield.The enantioselective hydrolysis of (±)-4-oxo-3,4-dihydro-2-chromen-3-yl acetate in various organic solvent-phosphate buffer (pH7) systems and enantioselective transesterification of (±)-3-hydroxy-2,3-dihydro-4H-chromen-4-one in organic solvents was investigated by screening a range of lipases. The lipase Amano PS, PPL, PLE and CCL-catalyzed asymmetric ester hydrolysis and transesterification afforded the enantiomers of 3-hydroxy-2,3-dihydro-4H-chromen-4-one and 4-oxo-3,4-dihydro-2-chromen-3-yl acetate with high enantiomeric excess (up to 97% ee) and in good yields.

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Hantzsch reaction of 3-(2-bromoacetyl)-4-hydroxy-chromen-2-one. Synthesis of 3-(thiazol-4-yl)-4-hydroxy coumarines
✍ S. Sukdolak; S. Solujić; N. Manojlović; N. Vuković; L. J. Krstić 📂 Article 📅 2004 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 143 KB

## Abstract 3‐Acetyl‐4‐hydroxy‐chromen‐2‐one (**1**) was brominated with phenyltrimethylammonium tribromide to afford 3‐(2‐bromoacetyl)‐4‐hydroxy‐chromen‐2‐one (**2**) whose reactions with thiourea, thioacetamide and ammonium dithiocarbamate gave respectively 3‐(2‐amino‐thiazol‐4‐yl)‐4‐hydroxy‐, 4‐