Diastereo- and enantioselective construction of an indole-based 2, 3-dihydrobenzofuran scaffold via catalytic asymmetric [3+2] cyclizations of quinone monoimides with 3-vinylindoles. Issue 14 (19th January 2016)

• Record Type: Journal Article
• Authors: Sun, Xiao-Xue; Zhang, Hong-Hao; Li, Guo-Hao; Meng, Li; Shi, Feng
• Is Part Of: Chemical communications. Volume 52:Issue 14(2016)
• Page Start: 2968
• Page End: 2971
• Publication Date: 2016-01-19
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c5cc09145d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The first catalytic asymmetric [3+2] cyclization of quinone monoimides with 3-vinylindoles has been established, which constructed a biologically important 2, 3-dihydrobenzofuran framework in high stereoselectivities (up to >95 : 5 dr, 96 : 4 er). Abstract : The first catalytic asymmetric [3+2] cyclization of quinone monoimides with olefins has been established, which employed 3-vinylindoles as a class of competent olefins and spiro-chiral phosphoric acid as a powerful chiral catalyst, leading to chemo-, diastereo- and enantioselective construction of a biologically important 2, 3-dihydrobenzofuran framework with optical purity (up to 99% yield, >95 : 5 dr, 96 : 4 er).