Catalytic Enantioselective Synthesis of Mariline A and Related Isoindolinones through a Biomimetic Approach. (2nd November 2017)

• Record Type: Journal Article
• Authors: Min, Chang; Lin, Yingfu; Seidel, Daniel
• Is Part Of: Angewandte Chemie. Volume 129:Number 48(2017)
• Page Start: 15555
• Page End: 15559
• Publication Date: 2017-11-02
• Subjects: Asymmetrische Katalyse -- Atropisomerie -- Brønsted-Säure-Katalyse -- Isoindolinone -- Marilin A; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201709182
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The catalytic enantioselective synthesis of isoindolinones was achieved through the condensation of 2‐acyl‐benzaldehydes and anilines. In the presence of 1 mol % of a chiral phosphoric acid catalyst, reactions reach completion within 10 min and provide products with up to 98 % ee . Anilines with an ortho t ‐butyl group form atropisomeric products, thereby enabling the simultaneous generation of axial and point chirality from two achiral substrates. This method was applied to the first synthesis of mariline A.