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Catalytic Enantioselective Synthesis of Mariline A and Related Isoindolinones through a Biomimetic Approach
Author(s) -
Min Chang,
Lin Yingfu,
Seidel Daniel
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709182
Subject(s) - enantioselective synthesis , catalysis , chirality (physics) , phosphoric acid , chemistry , condensation , combinatorial chemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , thermodynamics , quark
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.