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Asymmetric Construction of Six‐Membered Rings by Cyclization of Allenes with Dinuclear Gold Catalysis
Author(s) -
Qiu Youai,
Zhou Jing,
Li Junzhao,
Fu Chunling,
Guo Yinlong,
Wang Haoyang,
Ma Shengming
Publication year - 2015
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.201503179
Subject(s) - stereocenter , catalysis , chemistry , ring (chemistry) , chirality (physics) , combinatorial chemistry , stereochemistry , allene , medicinal chemistry , enantioselective synthesis , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , quark , nambu–jona lasinio model
A simple and efficient method for the synthesis of 1,4‐dihydroarenes by gold‐catalyzed 6‐ endo cyclization of benzylic allenes has been developed. Furthermore, asymmetric hydroarylation of enantioenriched allenes has been realized to offer a practical and convergent approach to aromatic ring‐fused six‐membered cycles containing a chiral stereocenter such as 1,4‐dihydronaphthalenes, 1,4‐dihydrodibenzo[ b , d ]thiophenes, and 4,7‐dihydrobenzo[ b ]thiophenes by applying dinuclear [(dppm)Au 2 Cl 2 ] [dppm=methylenebis(diphenylphosphane)] combined with AgOTf as the catalyst to ensure the high efficiency of chirality transfer. ESI‐MS has been applied to characterize some of the key reactive dinuclear gold intermediates successfully.