Highly Diastereoselective Synthesis of 2,2-Disubstituted Cyclopentane-1,3-diols via Stepwise Ketone Reduction Enabling Concise Chirality Construction
| Autor: | Bu Dandan, Jianjiong Li, Liangyan Zhu, Qin Wang, Jingyao Gong, Dunming Zhu, Jinhui Feng, Qiaqing Wu, Xi Chen, Hongliu Zhang |
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| Rok vydání: | 2020 |
| Předmět: |
inorganic chemicals
chemistry.chemical_classification Ketone 010405 organic chemistry Stereochemistry organic chemicals Organic Chemistry 010402 general chemistry 01 natural sciences 0104 chemical sciences Reduction (complexity) chemistry.chemical_compound Enantiopure drug chemistry Acetylation Biocatalysis polycyclic compounds heterocyclic compounds Stereoselectivity Cyclopentane Chirality (chemistry) |
| Zdroj: | The Journal of Organic Chemistry. 85:9599-9606 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.0c00851 |
| Popis: | A series of 2,2-disubstituted trans,cis-cyclopentane-1,3-diols were synthesized in >99% dr through enzymatic reduction of enantiopure 2,2-disubstituted 3-hydroxycyclopentane-1-ones, which were prepared by highly stereoselective enzymatic reduction of the corresponding cyclodiketones. For 2-benzyl-2-methyl-3-oxocyclopentyl acetate, acetylation of the hydroxyl group significantly affected the reduction stereoselectivity, giving trans,cis-, trans,trans-, and cis,cis-2-benzyl-2-methyl-cyclopentane-1,3-diols in stereomerically pure form. This efficient and environmentally friendly method provides a practical approach to the synthesis of these chiral building blocks in single stereoisomeric form, demonstrating the power of biocatalysis in the concise chirality construction of complex chiral molecules. |
| Databáze: | OpenAIRE |
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