NHC-Catalyzed Desymmetrization of N-Aryl Maleimides Leading to the Atroposelective Synthesis of N-Aryl Succinimides

Barik, S and Shee, S and Das, S and Gonnade, RG and Jindal, G and Mukherjee, S and Biju, AT (2021) NHC-Catalyzed Desymmetrization of N-Aryl Maleimides Leading to the Atroposelective Synthesis of N-Aryl Succinimides. In: Angewandte Chemie - International Edition, 60 (22). pp. 12264-12268.

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Abstract

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. © 2021 Wiley-VCH GmbH

Item Type:	Journal Article
Publication:	Angewandte Chemie - International Edition
Publisher:	John Wiley and Sons Inc
Additional Information:	The copyright for this article belongs to John Wiley and Sons Inc
Keywords:	Catalysis; Ketones; Temperature distribution, Biaryls; Desym-metrization; DFT study; Dialdehydes; Maleimides; N-heterocyclic carbenes; Rotation barriers; Temperature dependence, Synthesis (chemical)
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	05 Aug 2021 06:39
Last Modified:	05 Aug 2021 06:39
URI:	http://eprints.iisc.ac.in/id/eprint/69053

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