Base-controlled 1, 6-enyne-bicyclization: divergent synthesis of benzo[b]fluorenones and benzo[b]fluorenols. Issue 17 (28th April 2016)

• Record Type: Journal Article
• Authors: Hao, Wen-Juan; Zhou, Peng; Yang, Zheng; Jiang, Bo; Zhang, Jin-Peng; Tu, Shu-Jiang
• Is Part Of: Tetrahedron. Volume 72:Issue 17(2016)
• Page Start: 2206
• Page End: 2212
• Publication Date: 2016-04-28
• Subjects: 1, 6-Enyne-bicyclization -- Benzo[b]fluorenones -- Benzo[b]fluorenols -- Metal-free reaction -- Chemoselectivity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.03.026
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An interesting base-controlled protocol for the divergent and atom-economic synthesis of benzo[ b ]fluorenones and benzo[ b ]fluorenols with the great diversity in substitution patterns has been developed. Started from readily available 1, 6-enynes, good to excellent yields of the corresponding tetracyclic benzo[ b ]fluorenones and benzo[ b ]fluorenols can be chemoselectively achieved under metal-free conditions. Notably, only K2 CO3 or Et3 N was required as the promoter here and the reaction can work well in a high-selective manner. Graphical abstract: