Copper(i)-catalyzed [4 + 2] cycloaddition of aza-ortho-quinone methides with bicyclic alkenes. Issue 15 (29th March 2021)

• Record Type: Journal Article
• Authors: Lei, Lu; Liang, Yu-Feng; Liang, Cui; Qin, Jiang-Ke; Pan, Cheng-Xue; Su, Gui-Fa; Mo, Dong-Liang
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 15(2021)
• Page Start: 3379
• Page End: 3383
• Publication Date: 2021-03-29
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob00319d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient copper(i )-catalyzed [4 + 2] cycloaddition of aza- ortho -quinone methides (a o -QMs) and bicyclic alkenes to prepare tetrahydroquinoline-fused bicycles bearing multiple stereocenters in good yields is reported. Abstract : A variety of tetrahydroquinoline-fused bicycles bearing multiple stereocenters are prepared in good yields with high diastereoselectivity through Cu2 O-catalyzed [4 + 2] cycloaddition of aza- ortho -quinone methides (a o -QMs) with bicyclic alkenes. Mechanistic studies reveal that the Cu(i ) catalyst not only promotes the formation of a o -QMs through a radical process by single electron transfer but also accelerates [4 + 2] cycloaddition. The reaction was easily performed on gram scale and the obtained tetrahydroquinoline-fused bicycles can be converted to diverse tetrahydroquinoline scaffolds.