Merging singlet-oxygen induced furan oxidations with organocatalysis: synthesis of enantiopure cyclopentanones and hydrindanes
| Autor: | Georgios Vassilikogiannakis, Vasileios Tsopanakis, Tamsyn Montagnon, Dimitris Kalaitzakis, Manolis Sofiadis |
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| Rok vydání: | 2020 |
| Předmět: |
010405 organic chemistry
Singlet oxygen Organic Chemistry 010402 general chemistry Cyclopentanone 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Stereocenter chemistry.chemical_compound Enantiopure drug chemistry Cascade reaction Organocatalysis Furan Physical and Theoretical Chemistry |
| Zdroj: | Organicbiomolecular chemistry. 18(15) |
| ISSN: | 1477-0539 |
| Popis: | A new methodology is described herein which converts simple and readily accesible furan substrates into complex enantio-enriched carbocyclic skeletons through the implementation of a simple one-pot procedure. Singlet oxygen furan photoxygenation affords an enedione which then participates in an organocatalysed double-Michael reaction with an enal to furnish a cyclopentanone structure with up to four new contiguous stereogenic centres. The enantioselectivity and diastereoselectivity of this process are both excellent. If desired, further aldol-annulation steps can be appended to the cascade reaction sequence to afford key enantiopure hydrindane motifs. |
| Databáze: | OpenAIRE |
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