Diastereoselective construction of 3-aryl-substituted indolines via annulation of in situ generated p-quinone methides. Issue 48 (28th November 2019)

• Record Type: Journal Article
• Authors: Wang, Junwei; Pan, Xiang; Zhao, Lei; Zhao, Lin; Liu, Jian; Zhi, Ying; Wang, Ai; Zhao, Kun; Hu, Lihong
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 48(2019)
• Page Start: 10158
• Page End: 10162
• Publication Date: 2019-11-28
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02351h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A highly diastereoselective [4 + 1] annulation reaction of in situ generated p -quinone methides for the synthesis of 3-aryl-substituted indolines has been developed. Abstract : A highly diastereoselective [4 + 1] annulation reaction of in situ generated p -quinone methides for the synthesis of 3-aryl-substituted indolines has been developed. Employing commercial manganese dioxide as the oxidant, a series of ortho -tosylaminophenyl-substituted p -QMs could be generated in situ . This new protocol is based on an unprecedented 1, 6-conjugate addition/annulation cascade reaction, without the need for pre-synthesized p -QMs, and enables the easy preparation of a variety of 3-aryl-2, 3-dihydroindoles in good to excellent yields.