Organocatalytic Domino Michael/cyclization for the synthesis of highly substituted 4, 5-dihydrothiophenes

Ding, Chen-Hao; Dong, Jian-Lian; Yu, Li‐Si‐Han; Xie, Jian‐Hua

doi:10.1016/j.cclet.2017.08.048

Cited by 9 publications

(1 citation statement)

References 37 publications

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“…In the past years, organocatalysis, pioneered by Enders, List, Jørgensen, and MacMillan, has undoubtedly become one of the most efficient and reliable methods in modern organic synthesis . Catalyzed by chiral secondary amines and numerous variants, a variety of organocatalysis reactions could simultaneously form multiple bonds through a cascade sequence, exemplified with the construction of a six-membered carbo- and heterocycle skeleton using the organocatalytic Diels–Alder reaction (Figure a). Organocatalytic reactions are usually based on either a LUMO-lowering or HOMO-activation strategy, with the former using chiral Lewis acids to activate electron-deficient dienophiles and the latter using chiral aminocatalysts (enamine, dienamine, and trienamine) to activate alkyl and vinyl aldehydes and ketones .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized Bicyclo[2.2.2]octan-2-ones Skeleton via Tandem Process of Amino Acid Involved Formal [4 + 2] and Decarboxylative–Mannich Sequence

Mao

Nie

et al. 2021

J. Org. Chem.

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An efficient approach to a functionalized bicyclo[2.2.2]octan-2-one scaffold has been developed through a one-pot cascade process including amino acid involved successive Michael addition and decarboxylative−Mannich sequence. Starting from α,β-unsaturated ketones and amino acids, a series of desired products 7a−7m and 8a−8o were obtained with moderate yields. In addition, the tandem process was reasonably explained by the results of DFT calculations. Article pubs.acs.org/joc

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Section: Introductionmentioning

confidence: 99%

Synthesis of Functionalized Bicyclo[2.2.2]octan-2-ones Skeleton via Tandem Process of Amino Acid Involved Formal [4 + 2] and Decarboxylative–Mannich Sequence

Mao

Nie

et al. 2021

J. Org. Chem.

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TBHP‐Mediated Intermolecular Radical Coupling and Intramolecular Cyclization Cascade: Access to Furo[2,3‐b]quinoxalines and Their Photophysical Study

Ray,

Kumar,

Singh

et al. 2023

Adv Synth Catal

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A cascade one‐pot strategy to construct 31 examples of furo‐fused quinoxalines in up to 88% yields has been devised from readily accessible β‐ketothioamides and quinoxalin‐2‐ones in open flask at room temperature under TBHP mediated conditions. Mechanistic studies revealed that the overall reactivity relies on the seamless integration of intermolecular radical coupling and intramolecular cyclization via desulfhydration of C=S bond cleavage. Generation of H2S as the only by‐product makes this process highly attractive. Furthermore, the photophysical behavior of the furo‐fused quinoxalines has also been studied.

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Asymmetric Synthesis of Full Substituted Cyclohexa‐1,3‐dienes via Organocatalyzed Cascade Michael‐Cyclization of α, α‐Dicyanoalkenes with Nitroolefins

Cao,

Yin,

Xie

et al. 2024

ChemistrySelect

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An efficient organocatalytic cascade vinylogous Michael‐cyclization to construct the challenging full substituted cyclohexa‐1,3‐dienes has been developed. Catalyzed by the cinchona alkaloids‐derived thiourea VIII at −60 °C, the products were obtained as a single diastereomer with two contiguous stereocenters and more than four different useful functional groups in moderate to good yields and good to excellent enantioselectivities.

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Organocatalytic Domino Michael/cyclization for the synthesis of highly substituted 4, 5-dihydrothiophenes

Cited by 9 publications

References 37 publications

Synthesis of Functionalized Bicyclo[2.2.2]octan-2-ones Skeleton via Tandem Process of Amino Acid Involved Formal [4 + 2] and Decarboxylative–Mannich Sequence

Synthesis of Functionalized Bicyclo[2.2.2]octan-2-ones Skeleton via Tandem Process of Amino Acid Involved Formal [4 + 2] and Decarboxylative–Mannich Sequence

TBHP‐Mediated Intermolecular Radical Coupling and Intramolecular Cyclization Cascade: Access to Furo[2,3‐b]quinoxalines and Their Photophysical Study

Asymmetric Synthesis of Full Substituted Cyclohexa‐1,3‐dienes via Organocatalyzed Cascade Michael‐Cyclization of α, α‐Dicyanoalkenes with Nitroolefins

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