Organocatalytic Enantioselective Michael Addition of 3‐Indolinone‐2‐Carboxylates to Maleimides

Yarlagadda, Suresh; Reddy, Cheruku Ravindra; Ramesh, B.; Kumar, Gulshan; Sridhar, B.; Reddy, B. V. Subba

doi:10.1002/ejoc.201701670

Cited by 10 publications

(1 citation statement)

References 66 publications

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“…In 2018, Reddy et al . reported the asymmetric conjugate addition of 2‐substituted 3‐indolinones 68 with maleimides 3 using quinine squaramide catalyst 39 i (Scheme 43a) [61] . The reactions were proceeded well for various substrates to afford the products 69 contain a quaternary stereogenic centre with high yields, diastereoselectivities and enantioselectivities (up to 98 % yield, >99 : 1 d.r.…”

Section: Organocatalytic Asymmetric Conjugate Additions To Maleimidesmentioning

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: Organocatalytic Asymmetric Conjugate Additions To Maleimidesmentioning

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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Pd‐Catalyzed One‐Pot Insertion Reaction of Cyclic C‐Acylimines into Carbon‐Carbon σ‐Bonds for the Synthesis of Polyfunctional Indolin‐3‐ones from 2‐Alkynyl Arylazides and Aryl Ketones

Yong

Sheng

et al. 2018

Adv Synth Catal

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One‐Pot Asymmetric Oxidative Dearomatization of 2‐Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2‐Tetrasubstituted Indolin‐3‐Ones

Zhao

Yang

et al. 2022

Adv Synth Catal

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A one-pot approach for the asymmetric synthesis of C2-tetrasubstituted indolin-3-ones from 2substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2-substituted indoles using O 2 as green oxidant, and followed by an proline-promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2-tetrasubstituted indolin-3-ones were obtained in 35-86% yields, 2:1-> 20:1 dr and 48-99% ee. Moreover, the synthetic 2-tetrasubstituted indolin-3-ones could be easily transformed into 1H-[1,3] oxazino [3,4-a]indol-5(3H)-ones via a [4 + 1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi-drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively.

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Organocatalytic Enantioselective Michael Addition of 3‐Indolinone‐2‐Carboxylates to Maleimides

Cited by 10 publications

References 66 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

Pd‐Catalyzed One‐Pot Insertion Reaction of Cyclic C‐Acylimines into Carbon‐Carbon σ‐Bonds for the Synthesis of Polyfunctional Indolin‐3‐ones from 2‐Alkynyl Arylazides and Aryl Ketones

One‐Pot Asymmetric Oxidative Dearomatization of 2‐Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2‐Tetrasubstituted Indolin‐3‐Ones

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