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NHC‐Catalyzed Desymmetrization of N‐Aryl Maleimides Leading to the Atroposelective Synthesis of N‐Aryl Succinimides
Author(s) -
Barik Soumen,
Shee Sayan,
Das Soumik,
Gonnade Rajesh G.,
Jindal Garima,
Mukherjee Subrata,
Biju Akkattu T.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202016938
Subject(s) - succinimides , chemistry , aryl , desymmetrization , atropisomer , carbene , succinimide , axial chirality , organocatalysis , catalysis , organic chemistry , combinatorial chemistry , stereochemistry , enantioselective synthesis , alkyl
Although the construction of axially chiral C−C bonds leading to the atroposelective synthesis of biaryls and allied compounds are well‐known, the related synthesis of compounds bearing axially chiral C−N bonds are relatively rare. Described herein is the N‐heterocyclic carbene‐catalyzed atroposelective synthesis of N‐aryl succinimides having an axially chiral C−N bond via the desymmetrization of N‐aryl maleimides. The NHC involved intermolecular Stetter‐aldol cascade of dialdehydes with prochiral N‐aryl maleimides followed by oxidation afforded N‐aryl succinimides in good yields and ee values. Preliminary studies on rotation barrier for the C−N bond, the temperature dependence, and detailed DFT studies on mechanism are also provided.