Enantioselective Bifunctional Ammonium Salt‐Catalyzed Syntheses of 3‐CF3S‐, 3‐RS‐, and 3‐F‐Substituted Isoindolinones. Issue 7 (17th February 2021)

• Record Type: Journal Article
• Authors: Eitzinger, Andreas; Otevrel, Jan; Haider, Victoria; Macchia, Antonio; Massa, Antonio; Faust, Kirill; Spingler, Bernhard; Berkessel, Albrecht; Waser, Mario
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 7(2021)
• Page Start: 1955
• Page End: 1962
• Publication Date: 2021-02-17
• Subjects: Organocatalysis -- Asymmetric phase-transfer catalysis -- Bifunctional catalysis -- Heterofunctionalization -- Organofluorine chemistry; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100029
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: We herein report the ammonium salt‐catalyzed synthesis of chiral 3, 3‐disubstituted isoindolinones bearing a heteroatom functionality in the 3‐position. A broad variety of differently substituted CF3 S‐ and RS‐derivatives were obtained with often high enantioselectivities when using Maruoka's bifunctional chiral ammonium salt catalyst. In addition, a first proof‐of‐concept for the racemic synthesis of the analogous F‐containing products was obtained as well, giving access to one of the rare examples of a fairly stable α‐F‐α‐amino acid derivative. Abstract :