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Catalytic Enantioselective Michael Addition Reactions of Tertiary Enolates Generated by Detrifluoroacetylation
Author(s) -
Zhu Yi,
Zhang Wenzhong,
Mei Haibo,
Han Jianlin,
Soloshonok Vadim A.,
Pan Yi
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702091
Subject(s) - stereocenter , enantioselective synthesis , catalysis , michael reaction , chemistry , benzene , molecule , carbon fibers , quaternary carbon , diamine , organic chemistry , materials science , composite number , composite material
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 (1 S ,2 S )‐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.