Asymmetric Synthesis of Cyclopentane‐Substituted Oxindoles via Organocatalytic Desymmetrization of Cyclopent‐4‐ene‐1, 3‐diones. Issue 11 (8th May 2017)

• Record Type: Journal Article
• Authors: Zhi, Ying; Zhao, Kun; Wang, Ai; Englert, Ullrich; Raabe, Gerhard; Enders, Dieter
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 11(2017)
• Page Start: 1867
• Page End: 1871
• Publication Date: 2017-05-08
• Subjects: asymmetric synthesis -- cyclopent-4-ene-1, 3-diones -- desymmetrization -- organocatalysis -- oxindoles; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201700358
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The highly enantioselective desymmetrization of prochiral cyclopent‐4‐ene‐1, 3‐diones has been developed via an organocatalytic Michael reaction. This desymmetrization protocol is efficiently catalyzed by 10 mol% of a bifunctional squaramide, offering a short entry into a series of cyclopentane‐substituted oxindoles bearing two quaternary and one tertiary stereocenters in good yields and high stereoselectivities. Abstract :