Diastereoselective synthesis of spiro-cyclopropanyl-cyclohexadienones via direct sulfide-catalyzed [2 + 1] annulation of para-quinone methides with bromides. Issue 22 (22nd May 2020)

• Record Type: Journal Article
• Authors: Su, Yingpeng; Zhao, Yanan; Chang, Bingbing; Ling, Qinqin; Feng, Yawei; Zhao, Xiaolong; Huang, Danfeng; Wang, Ke-Hu; Huo, Congde; Hu, Yulai
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 22(2020)
• Page Start: 4257
• Page End: 4266
• Publication Date: 2020-05-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob00778a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A sulfide-catalyzed [2 + 1] annulation of para -quinone methides with diverse bromides was disclosed to access appealing spiro-cyclopropanyl-cyclohexadienones with high diastereoselectivity. Abstract : An efficient sulfide-catalyzed [2 + 1] annulation of para -quinone methides ( p -QMs) with diverse bromides has been achieved. This catalytic strategy provides an efficient and straightforward protocol for accessing a variety of spiro-cyclopropanyl-cyclohexadienone compounds in good to excellent yields (64% to 96% yields) with outstanding diastereoselectivities (>20 : 1 dr), displaying good functional group tolerance as well as gram-scale capacity.