Chiral N-Heterocyclic-Carbene-Catalyzed Cascade Asymmetric Desymmetrization of Cyclopentenediones with Enals: Access to Optically Active 1,3-Indandione Derivatives
| Autor: | Xing-Wang Wang, Zheng Wang, Jie-Qiang Yu, Jun-Bo Chen, Xiao-Peng Yang, Hao-Peng Lv, Bing-Bing Sun, Jun-Qi Zhang, Jia-Ming Hu |
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| Rok vydání: | 2019 |
| Předmět: |
Annulation
1 3-Indandione 010405 organic chemistry Organic Chemistry Aromatization 010402 general chemistry 01 natural sciences Biochemistry Desymmetrization Combinatorial chemistry 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry Aldol reaction Functional group Physical and Theoretical Chemistry Carbene |
| Zdroj: | Organic Letters. 21:8582-8586 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.9b03178 |
| Popis: | A chiral N-heterocyclic-carbene-catalyzed cascade asymmetric desymmetrization reaction of cyclopentenediones with enals has been successfully initiated, followed with tandem aldol annulation, aromatization, as well as sequential methylation. The reactions proceeded well under mild reaction conditions, with broad substrate scope and good functional group tolerance, providing a rapid access to highly functionalized chiral 2,2-disubstituted 1,3-indandione derivatives containing an all-carbon quaternary stereogenic center in moderate to good yields with high enantioselectivities. |
| Databáze: | OpenAIRE |
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