Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Catalytic Enantioselective Michael Addition Reactions of Tertiary Enolates Generated by Detrifluoroacetylation

Catalytic Enantioselective Michael Addition Reactions of Tertiary Enolates Generated by Detrifluoroacetylation
Wenzhong Zhang, Yi Zhu, Jianlin Han, Haibo Mei, Yi Pan, Vadim A. Soloshonok
This work describes, for the first time, Michael addition reactions of tertiary fluoro-enolates in situ generated by detrifluoroacetylation with 1-(1-(phenylsulfonyl) vinylsulfonyl)benzene. Excellent enantioselectivity and chemical yields were achieved with application of catalysts (10 mol %) derived from Cu(OTf)2 and (1S,2S)-1,2-diphenylethane-1,2-diamine. These reactions show a considerable degree of structural generality and allow the preparation of new types of biologically relevant molecules that contain quaternary C−F stereogenic carbon atoms and feature five-, six-, or seven-membered rings as well as heterocyclic 3-fluoro-2,3-dihydrochromen-4-one moieties. All-in-One! An enantioselective Cu-catalyzed cascade detrifluoroacetylation of 2-fluoro-1,3-di-ketones/hydrates and Michael addition to sulfonated olefins was discovered, advantageous to the traditional application of α-fluoro-ketones. Anthracenyl-substituted 1,2-diphenylethane-1,2-diamine was found as the optimal chiral ligand to catalyze the reaction to afford products containing a quaternary C−F stereogenic carbon with excellent enantioselectivity and chemical yields.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702091

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