Straightforward access to densely substituted chiral succinimides through enantioselective organocatalyzed Michael addition of α-alkyl-cyclic ketones to maleimides

Lai, Wei; Chen, Li; Bideau, Franck Le; Retailleau, Pascal; Dumas, Françoise

doi:10.1039/c9qo01463b

Cited by 9 publications

(1 citation statement)

References 45 publications

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“…Bideau, Dumas and co-workers explored microwave triggered organocatalytic asymmetric direct conjugate addition of α-alkyl cyclic ketones 43 with unprotected or N-protected maleimides 3 (Scheme 32). [44] The reaction proceeded very smoothly using a simple chiral amine catalyst 12 l. In 20 mol % of catalyst 12 l and 4-nitro benzoic acid as an additive, the reaction completed in 12 h under microwave irradiation to afford the desired products 44 or 45 with moderate to very high yields, diastereoselectivities and enantioselectivities (up to 79 % yield, > 98 : 2 d.r., 99 % ee). The reaction was assumed to proceed via the enamine formation of α-alkyl cyclic ketones with the chiral catalyst and the simultaneous activation of maleimide through hydrogen bonding in presence of the additive 4-nitro benzoic acid.…”

Section: Using Chiral Amine or Amino Acidsmentioning

confidence: 99%

Recent Advancement on the Organocatalyzed Asymmetric Conjugate Addition using Maleimide as a Potential Substrate

Jana,

Mondal,

Halder

et al. 2023

Asian J Org Chem

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Asymmetric organocatalytic 1,4‐conjugate addition is considered as an effective, powerful and sustainable method for carbon‐carbon bond formation. The core structure of maleimides or succinimides were found in several bioactive molecules as well as in natural products. Unprotected and protected maleimides were employed as an electrophile to construct novel succinimide based organic molecules. The rapid development of several new effective and prominent methodologies encourages us to write a review by summarizing the recent updates. In this review, we present an overview of the past 10 years progress on the asymmetric organocatalytic 1,4 conjugate additions using unprotected and protected maleimides. Special attention has been paid classifying the types of nucleophiles as well as catalysts employed for this asymmetric transformation along with substrate scope, limitation, mechanism, and synthetic utilities for each reaction. Knowing the versatility of maleimides, this review will encourage active researchers around the globe to put more efforts on the development of new methodologies including asymmetric photo redox catalysis for further functionalization of maleimides.

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Section: Using Chiral Amine or Amino Acidsmentioning

confidence: 99%

Recent Advancement on the Organocatalyzed Asymmetric Conjugate Addition using Maleimide as a Potential Substrate

Jana,

Mondal,

Halder

et al. 2023

Asian J Org Chem

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New Synthetic Approaches for the Construction of Enantioenriched Molecules Bearing Quaternary Stereocenters

Sun,

Liu,

Shi

et al. 2024

Adv Synth Catal

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Optically active molecule architectures stand as an important class of organic compounds and occupy a key role in academic and industrial communities. Particularly, the molecules bearing quaternary carbon are of vital importance because of its favorable conformation and valuable three‐dimensional molecules, which frequently play a key role in a broad spectrum of functional materials, pharmaceutical relevant natural molecules, and agrochemicals. Over the past few decades, a large amount of synthetic strategies for the enantioselective construction of compounds with chiral quaternary carbon centers have been the focus of a number of research initiatives. In this review, the state‐of‐the‐art toward the synthesis of enantioenriched molecules bearing quaternary stereocenters are summarized, which could be segmented into four categories: 1) Construction of optically active quaternary carbon centers by addition to prochiral sp2 carbon; 2) Construction of optically active all‐carbon quaternary stereocenters via substitution at non‐chiral tetra‐substituted carbon; 3) Construction of optically active all‐carbon quaternary stereocenters via kinetic resolution; 4) Construction of optically active all‐carbon quaternary stereocenters via desymmetrization reactions.

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Peptide‐Catalyzed Stereoselective Conjugate Addition Reaction of Aldehydes to C‐Substituted Maleimides

Vastakaite

Grünenfelder

Wennemers

2022

Chemistry A European J

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Catalytic stereoselective additions with maleimides are useful one‐step reactions to yield chiral succinimides, molecules that are widespread among therapeutically active compounds but challenging to prepare when the maleimide is C‐substituted. We present the tripeptide H‐Pro‐Pro‐Asp‐NHC12H25 as a catalyst for conjugate addition reactions between aldehydes and C‐substituted maleimides to form succinimides with three contiguous stereogenic centers in high yields and stereoselectivities. The peptidic catalyst is so chemoselective that no protecting group is needed at the imide nitrogen of the maleimides. Derivatization of the succinimides was straightforward and provided access to chiral pyrrolidines, lactones, and lactams. Kinetic studies, including a Hammett plot, provided detailed insight into the reaction mechanism.

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Straightforward access to densely substituted chiral succinimides through enantioselective organocatalyzed Michael addition of α-alkyl-cyclic ketones to maleimides

Abstract: A simple, cheap and unchanged organocatalytic system provides efficient access to densely substituted chiral succinimides bearing QCC–TCC vicinal stereocenters from unreactive α-alkyl cyclic ketones and maleimides.

Cited by 9 publications

References 45 publications

Recent Advancement on the Organocatalyzed Asymmetric Conjugate Addition using Maleimide as a Potential Substrate

Recent Advancement on the Organocatalyzed Asymmetric Conjugate Addition using Maleimide as a Potential Substrate

New Synthetic Approaches for the Construction of Enantioenriched Molecules Bearing Quaternary Stereocenters

Peptide‐Catalyzed Stereoselective Conjugate Addition Reaction of Aldehydes to C‐Substituted Maleimides

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