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Mg II ‐Mediated Catalytic Asymmetric Dearomatization (CADA) Reaction of β‐Naphthols with Dialkyl Acetylenedicarboxylates
Author(s) -
Wang Linqing,
Yang Dongxu,
Li Dan,
Wang Pengxin,
Wang Kezhou,
Wang Jie,
Jiang Xianxing,
Wang Rui
Publication year - 2016
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.201601399
Subject(s) - intramolecular force , catalysis , chemistry , hydride , tandem , combinatorial chemistry , medicinal chemistry , cascade reaction , organic chemistry , hydrogen , materials science , composite material
Abstract A Mg II ‐mediated catalytic asymmetric dearomatization (CADA) reaction of β‐naphthols has been developed. The reaction proceeds under ambient temperature and give a series of chiral trisubstituted olefins with good chemoselectivities, Z / E ratios, and excellent enantioselectivities. A fluorinated β‐naphthol was designed to generate chiral organofluorine skeletons through the current CADA reaction. Moreover, an interesting tandem cyclization reaction was observed in the following transformation process through an undiscovered intramolecular hydride transfer pathway.