Catalytic Enantioselective Synthesis of MarilineA 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 1mol% of a chiral phosphoric acid catalyst, reactions reach completion within 10min and provide products with up to 98% ee. Anilines with an ortho...

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Bibliographic Details
Published in:Angewandte Chemie 2017-11, Vol.129 (48), p.15555
Main Authors: Min, Chang, Lin, Yingfu, Seidel, Daniel
Format: Article
Language:ger
Subjects:
Biomimetics
Catalysis
Chemical synthesis
Chemistry
Chirality
Condensates
Enantiomers
Phosphoric acid
Substrates
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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 1mol% of a chiral phosphoric acid catalyst, reactions reach completion within 10min 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 marilineA.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201709182