Synthesis of Chiral Six-Membered Carbocyclic Purine Nucleosides via Organocatalytic Enantioselective [3 + 3] Annulation
| Autor: | Hai-Ming Guo, Ke-Xin Huang, Zhang Qiying, Ming-Sheng Xie, Hong-Ying Niu, Gui-Rong Qu |
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| Rok vydání: | 2018 |
| Předmět: |
Purine
Annulation 010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis Stereocenter chemistry.chemical_compound Direct route chemistry Physical and Theoretical Chemistry Nucleoside |
| Zdroj: | Organic Letters. 20:5398-5401 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A direct route to chiral six-membered carbocyclic purine nucleoside analogues with three chiral stereocenters, including a chiral tetrasubstituted carbon center, via a highly enantioselective [3 + 3] annulation has been established. With the application of Takemoto's catalyst, various chiral six-membered carbocyclic purine nucleoside analogues were obtained in high yields (up to 89%) with moderate to good diastereoselectivities (up to 90:10 dr) and excellent enantioselectivities (92-98% ee). Furthermore, diverse chiral six-membered carbocyclic purine nucleoside analogues were generated by simple transformations. |
| Databáze: | OpenAIRE |
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