期刊
MOLECULES
卷 27, 期 20, 页码 -出版社
MDPI
DOI: 10.3390/molecules27206981
关键词
enolization; chemoselectivity; regioselectivity; enantioselectivity; fluorination
资金
- National Science Foundation of China (NSFC) [21971193]
- Fundamental Research Funds for the Central Universities
The utilization of 6,6-dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one, derived from an unsymmetrical 4,4-dimethylcyclohexane-1,3-dione, in iridium-catalyzed allylic enolization is achieved under mild conditions. The presence of a quaternary carbon and adjustment of reaction conditions enable high selectivities in terms of chemoselectivity, regioselectivity, and enantioselectivity. This method provides substituted 2-(but-3-en-2-yl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-ones in good to high yields with excellent chemo-, regio-, and enantioselectivities. Additionally, the formation of chiral carbon-fluorine bonds is induced by an adjacent chiral carbon center.
The utilization of 6,6-dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one made from an unsymmetrical 4,4-dimethylcyclohexane-1,3-dione in iridium-catalyzed allylic enolization involving keto-enol isomerization is accomplished under mild conditions. The chemoselectivity, regioselectivity, and enantioselectivity are facilitated by the quaternary carbon and adjusting the reaction conditions. This method provides the substituted 2-(but-3-en-2-yl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-ones in good to high yields with high level of chemo-, regio-, and enantioselectivities. The chiral carbon-fluorine bond formation is induced by an adjacent chiral carbon center of the allylated 3-hydroxy-6,6-dimethylcyclohex-2-en-1-one, as well.
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