Deracemization of α-monosubstituted cyclopentanones in the presence of a TADDOL-type host molecule
| Autor: | Minami Ito, Tetsuto Tsunoda, Hiroto Kaku, Mitsuyo Horikawa |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Aqueous solution
010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Optically active 010402 general chemistry Cyclopentanone 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Solvent chemistry.chemical_compound Molecular recognition Phase (matter) Yield (chemistry) Drug Discovery Molecule |
| Zdroj: | Tetrahedron. 74:124-129 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2017.11.045 |
| Popis: | Racemic α-monosubstituted cyclopentanones were converted to optically active forms by a thermodynamically controlled deracemization using TADDOL-type host molecule 1 in alkaline aqueous MeOH. The efficiency of this conversion was strongly influenced by the ratio of the solvent components (H2O/MeOH) and the functionality and architecture of the α-side-chain on the cyclopentanones. For example, (R)-2-(2-benzyloxyethyl)cyclopentanone (9) was obtained in 89% yield with 97% ee using a 7:3 mixture of H2O/MeOH as the solvent. X-ray analytical studies were also carried out and disclosed the nature of this chiral molecular recognition process in the solid phase. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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