title: Asymmetric Construction of Six-Membered Rings by Cyclization of Allenes with Dinuclear Gold Catalysis.
abstract: 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)Au2 Cl2 ] [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.
authors.affiliation: Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P. R. China).
authors.forename: Youai
authors.initials: Y
authors.lastname: Qiu
authors.affiliation: Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P. R. China).
authors.forename: Jing
authors.initials: J
authors.lastname: Zhou
authors.affiliation: Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P. R. China).
authors.forename: Junzhao
authors.initials: J
authors.lastname: Li
authors.affiliation: Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P. R. China).
authors.forename: Chunling
authors.initials: C
authors.lastname: Fu
authors.affiliation: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032, Shanghai (P. R. China).
authors.forename: Yinlong
authors.initials: Y
authors.lastname: Guo
authors.affiliation: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032, Shanghai (P. R. China). haoyangwang@sioc.ac.cn.
authors.forename: Haoyang
authors.initials: H
authors.lastname: Wang
authors.affiliation: Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang (P. R. China). masm@sioc.ac.cn.|Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032, Shanghai (P. R. China). masm@sioc.ac.cn.
authors.forename: Shengming
authors.initials: S
authors.lastname: Ma
keywords: allenes; chirality transfer; cyclization; gold; homogeneous catalysis