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Gold‐Catalyzed Tandem Cyclization/Cycloaddition Reaction of Enynones: Highly Regioselective Synthesis of Oxabicyclic Compounds and Naphthyl Ketones
Author(s) -
Song XianRong,
Xia XiaoFeng,
Song Bo,
Tian Xiang,
Zhu HaiTiao,
Zhou AnXi,
Liu XueYuan,
Liang YongMin
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300118
Subject(s) - regioselectivity , cycloaddition , chemistry , catalysis , phosphine , ketone , medicinal chemistry , biphenyl , organic chemistry
A gold‐catalyzed benzannulation of enynones for synthesizing oxabicyclic compounds and naphthyl ketones with high regioselectivity has been developed. Divergent products can be obtained from the same substrates through different types of cycloaddition. In this reaction, enynones were selectively transformed through [3+2] cycloadditions to give oxabicycles 2 in the presence of [L 3 AuCl] (L 3 =[tris( para ‐trifluoromethylphenyl)phosphine], 5 mol %). When [L 2 (CNCH 3 )Au]SbF 6 (L 2 =[2‐(di‐ tert ‐butylphosphino)biphenyl]) was used as the catalyst, the [4+2] cycloaddition naphthyl ketone products dihydrobenzo[ f ]isoquinolines 3 were obtained. The value of this method is indicated by the applicability of various enynones substrates and the highly regioselective synthesis of two potentially useful polycyclic compounds.