Catalytic Enantioselective Synthesis of Mariline A and Related Isoindolinones through a Biomimetic Approach

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 o...

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Published inAngewandte Chemie Vol. 129; no. 48; pp. 15555 - 15559
Main Authors Min, Chang, Lin, Yingfu, Seidel, Daniel
Format Journal Article
LanguageEnglish
Published 27.11.2017
Subjects
Asymmetrische Katalyse
Atropisomerie
Brønsted-Säure-Katalyse
Isoindolinone
Marilin A
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Summary: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. Katalytisch kondensiert: Die enantioselektive Synthese von Isoindolinonen gelingt durch die Kondensation von 2‐Acylbenzaldehyden mit Anilinen. In Gegenwart von 1 Mol‐% eines chiralen Phosphorsäure‐Katalysators sind die Umsetzungen nach 10 Minuten abgeschlossen. Die Produkte werden mit bis zu 98 % ee erhalten. Aniline mit ortho‐tert‐Butyl‐Gruppe bilden atropisomere Produkte. Die Methode wurde in der ersten Synthese von Marilin A angewendet.
Bibliography:These authors contributed equally to this work.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201709182