Asymmetric Construction of Six‐Membered Rings by Cyclization of Allenes with Dinuclear Gold Catalysis. Issue 45 (21st September 2015)

• Record Type: Journal Article
• Authors: Qiu, Youai; Zhou, Jing; Li, Junzhao; Fu, Chunling; Guo, Yinlong; Wang, Haoyang; Ma, Shengming
• Is Part Of: Chemistry. Volume 21:Issue 45(2015)
• Page Start: 15939
• Page End: 15943
• Publication Date: 2015-09-21
• Subjects: allenes -- homogeneous catalysis -- chirality transfer -- cyclization -- gold; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201503179
• Languages: English
• ISSNs: 0947-6539

Abstract

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. 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 catalyzed by dinuclear [(dppm)Au2 Cl2 ] combined with AgOTf offers a convergent approach to aromatic ring‐fused six‐membered cycles containing a chiral stereocenter (see scheme; dppm=methylenebis(diphenylphosphane).