Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization

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 enanti...

Full description

Saved in:
Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 27; no. 20; p. 6981
Main Authors Wang, Xiao-Lin, Chen, Ji-Teng, Zheng, Sheng-Cai, Zhao, Xiao-Ming
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 17.10.2022
MDPI
Subjects
Catalysis
chemoselectivity
Diketones
Enantiomers
enantioselectivity
enolization
fluorination
Fluorine
Isomerization
Ligands
Regioselectivity
Solvents
Online AccessGet full text

Cover

More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27206981