N‐Heterocyclic Carbene‐Catalyzed Umpolung Formal [3+3] Cycloaddition of Enals with Isatogens: Access to Fused Indolin‐3‐ones with a Tetrasubstituted Carbon Stereocenter

Xu, Junyu; Hu, Sheng-Zhi; Lu, Yun; Dong, Ying; Tang, Weifang; Lü, Tao; Du, Ding

doi:10.1002/adsc.201401070

Cited by 42 publications

(7 citation statements)

References 66 publications

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“…In 2015, the Du group demonstrated an effective strategy for the synthesis of fused indolin-3-ones with a tetrasubstituted carbon stereocenter via NHC-catalyzed umpolung [3+3] annulation of enals 132 with isatogens 203. 57 The reaction proceeded with moderate to high yields and diastereoselectivity favoring the cis-isomer. The author proposed that the Breslow intermediate 206, generated by the combination of enal with NHC, can form hydrogen-bonding interaction with 203, which can reasonably explain the predominant formation of the syn-products (Scheme 42).…”

Section: Synthesis Of Heterocycles Containing Two or More Heteroatomsmentioning

confidence: 97%

Organocatalyzed [3+3] Annulations for the Construction of Heterocycles

Zhu¹,

Huang

2020

Synthesis

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Six-membered heterocyclic systems are widely distributed in many natural products and pharmaceuticals, and the construction of highly functionalized six-membered heterocyclic compounds is an important topic in modern organic synthesis. Organocatalyzed [3+3] annulations represents an important method for assembling a substantial variety of six-membered cycles that contain one or more heteroatoms. This review describes the development of organocatalyzed [3+3] annulations for the synthesis of six-membered heterocycles, including organocatalysis using secondary amines, tertiary amines, phosphines, chiral phosphoric acids and N-heterocyclic carbenes.1 Introduction2 Secondary Amine Catalyzed [3+3] Annulations2.1 Synthesis of Nitrogen Heterocycles2.2 Synthesis of Oxygen Heterocycles2.3 Synthesis of Sulfur Heterocycles3 Tertiary Amine Catalyzed [3+3] Annulations3.1 Catalysis through Multiple Hydrogen-Bonding Interactions3.2 Catalysis of Tertiary Amines as Lewis Bases4 Phosphine-Catalyzed [3+3] Annulations4.1 Synthesis of Nitrogen Heterocycles4.2 Synthesis of Oxygen Heterocycles4.3 Synthesis of Heterocycles Containing Two or More Heteroatoms5 Chiral Phosphoric Acid Catalyzed [3+3] Annulations5.1 Synthesis of Nitrogen Heterocycles5.2 Synthesis of Heterocycles Containing Two or More Heteroatoms6 N-Heterocyclic Carbene Catalyzed [3+3] Annulations6.1 Synthesis of Nitrogen Heterocycles6.2 Synthesis of Oxygen Heterocycles6.3 Synthesis of Heterocycles Containing Two or More Heteroatoms7 Conclusion and Outlook

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Section: Synthesis Of Heterocycles Containing Two or More Heteroatomsmentioning

confidence: 97%

Organocatalyzed [3+3] Annulations for the Construction of Heterocycles

Zhu¹,

Huang

2020

Synthesis

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“…In 2015, Dua and colleagues reported an interesting N‐heterocyclic carbene (NHC) catalyzed umpolung cycloaddition of enals 31 with isatogens 32 to obtain tetrasubstituted fused indolin‐3‐ones 33/34 via sequential ring‐opening/reduction/ring‐closing process (Scheme 10). [14a] Idea of this reaction originated from Scheidt's work on the NHC‐catalyzed formal [3+3] cycloaddition of acyclic nitrones with enals, followed by nucleophilic ring‐opening of the six‐membered adducts to yield possible γ‐amino acids [14b] . The reactions usually go smoothly with moderate to high yields and with decent diastereoselectivity.…”

Section: Cycloaddition Reactionsmentioning

confidence: 99%

Synthetic Applications of Ambiphilic C‐acylimines in Organic Synthesis

2022

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C‐acylimines are generally obtained through condensation/dehydration of simple and readily available glyoxals and amines. The structure resembles naturally occurring biological substances due to the presence of the imino group (−N=C−). Chemically, C‐acylimines exhibit ambiphilic reactivity, and hence, their synthetic chemistry becomes more attractive and viable for the synthesis of various aza‐cyclic/heterocyclic compounds, including their asymmetric counterpart. Therefore, many synthetic methodologies were developed from these readily preparable C‐acylimines. Surprisingly, there is no account/review available on this specific topic. Hence we present here an account of all the synthetic endeavours developed from C‐acylimines to synthesize small molecules and complex systems using various strategies.

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“…1 H -Pyrrol-3(2 H )-one derivatives have received considerable attention because they widely exist in natural products and biologically active compounds . Due to their importance, many efforts have been undertaken for their syntheses and modifications . The main synthetic strategies occur by three routes: (1) dimerization of enamines (mediated by hypervalent iodine(III) reagent, TBHP/TBAI system; catalyzed by p -TsOH, Cu(TFA) 2 ); (2) cyclization of corresponding open-chain precursors (catalyzed by gold, platinum, copper; treated with I 2 , TEMPO, thermal cyclization); (3) transformations based on indolin-3-ones or indoles including Michael addition reaction, annulation reaction, rearrangement reaction, and oxidation reaction .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1H-Pyrrol-3(2H)-ones via Three-Component Reactions of 2,3-Diketo Esters, Amines, and Ketones

2018

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An efficient one-pot, three-component reaction of 2,3-diketo esters with amines and ketones has been developed for the synthesis of 1 H-pyrrol-3(2 H)-ones. By using trifluoroacetic acid (TFA) as the additive and acetonitrile (MeCN) as the solvent, this convenient method provides a library of 1 H-pyrrol-3(2 H)-ones in moderate to good yields. The simple protocol features readily available starting materials, a straightforward process, good functional group tolerance, and broad substrate scope.

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N‐Heterocyclic Carbene‐Catalyzed Umpolung Formal [3+3] Cycloaddition of Enals with Isatogens: Access to Fused Indolin‐3‐ones with a Tetrasubstituted Carbon Stereocenter

Cited by 42 publications

References 66 publications

Organocatalyzed [3+3] Annulations for the Construction of Heterocycles

Organocatalyzed [3+3] Annulations for the Construction of Heterocycles

Synthetic Applications of Ambiphilic C‐acylimines in Organic Synthesis

Synthesis of 1H-Pyrrol-3(2H)-ones via Three-Component Reactions of 2,3-Diketo Esters, Amines, and Ketones

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