N-Heterocyclic Carbene-Catalyzed Formal [3 + 2] Annulation of α-Bromoenals with 3-Aminooxindoles: A Stereoselective Synthesis of Spirooxindole γ-Butyrolactams

Jiang, Delu; Dong, Shuding; Tang, Weifang; Lü, Tao; Du, Ding

doi:10.1021/acs.joc.5b02188

Cited by 71 publications

(15 citation statements)

References 60 publications

(19 reference statements)

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“…In 2015, Lu and Du reported an NHC catalysed [3 + 2] annulation of 2-bromoenals with 3-aminooxindoles (Scheme 44A). 207 Using NHC cat. 44 Lu and Du achieved high enantioselectivity of the spiropyrrolidinone product.…”

Section: [3 + 2]-cycloadditionmentioning

confidence: 99%

Stereoselective synthesis and applications of spirocyclic oxindoles

2021

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Section: [3 + 2]-cycloadditionmentioning

confidence: 99%

Stereoselective synthesis and applications of spirocyclic oxindoles

2021

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“…After Yao’s work [ 61 ], Du and colleagues reported a formal [3+2] annulation of α-bromoenals 76 -derived α,β-unsaturated acyl azoliums with 3-amino-oxindoles 77 via NHC organocatalysis. The functionalized spirooxindole γ-butyrolactams 78 are synthesized with high diastereoselectivities (up to >95:5 dr) and enantioselectivities (86–95% ee) ( Scheme 24 ) [ 62 ].…”

Section: Nhc-catalyzed Synthesis Of Spiroheterocyclesmentioning

confidence: 99%

Recent Advances in the Synthesis of Spiroheterocycles via N-Heterocyclic Carbene Organocatalysis

et al. 2017

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Spiroheterocycles are regarded as a privileged framework because of their wide distribution in various natural products and synthetic molecules and promising bioactivities. This review focuses on the recent advances in the synthesis of spiroheterocycles by using the strategy of N-heterocyclic carbene (NHC) organocatalysis, and is organized based on the stereoselectivity and the reactive intermediates. According to the stereochemistry, this review was divided into two main parts, covering racemic and enantioselective versions. In each part, we firstly describe the synthetic transformations using nucleophilic Breslow intermediates, and then discuss the reactions that employ electrophilic acylazolium or radical cation intermediates. With those distinct catalytic activation modes of NHC organocatlysis, we expect this synthetic protocol will possibly produce new molecules with structural novelty and complexity, which may warrant further research in the field of drug discovery.

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“…Lu and Du described NHC 145 ‐catalyzed formal [3+2] annulation of α‐bromoenals with 3‐aminooxindole 146 , which proved to be a stereoselective synthetic approach to spirooxindole γ‐butyrolactam 147 (Scheme ) . In this reaction, 3‐aminooxindole 146 serves as a 1,2‐bisnucleophile to undergo formal [3+2] annulation with the generated α,β‐unsaturated acyl azolium intermediate.…”

Section: Benzaldo‐x Bifunctional Building Blocks and Their Heterocyclmentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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N-Heterocyclic Carbene-Catalyzed Formal [3 + 2] Annulation of α-Bromoenals with 3-Aminooxindoles: A Stereoselective Synthesis of Spirooxindole γ-Butyrolactams

Cited by 71 publications

References 60 publications

Stereoselective synthesis and applications of spirocyclic oxindoles

Stereoselective synthesis and applications of spirocyclic oxindoles

Recent Advances in the Synthesis of Spiroheterocycles via N-Heterocyclic Carbene Organocatalysis

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

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