Progress in Asymmetric Organocatalyzed Michael Addition/Hemi-aminoacetalization/Acylimminium-Cyclization Cascade Reactions

陈杰,; 刘钦,; 戴小鸯,; 聂凛凛,; 房辉辉,; 吴小余,

doi:10.6023/cjoc201208032

Cited by 8 publications

(4 citation statements)

References 4 publications

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“…As a result, over the past several years, many elegant strategies have been established for the fast and efficient construction of indoloquinolizidine scaffold from simple starting materials. 23 Inspired by these achievements, we . 24 Initially, Michael addition of 31 to 6 generated chiral hemiacetal 32 in the presence of secondary amine 33 through iminium activation.…”

Section: Accounts Of Chemical Researchmentioning

confidence: 96%

“…As a result, over the past several years, many elegant strategies have been established for the fast and efficient construction of indoloquinolizidine scaffold from simple starting materials. 23 Inspired by these achievements, we developed a cascade reaction employing α-oxo-γ-butyrolactam 31 as a new N-containing pronucleophile for the synthesis of the butyrolactam-fused indoloquinolizidine scaffold (Scheme 7). 24 Initially, Michael addition of 31 to 6 generated chiral hemiacetal 32 in the presence of secondary amine 33 through iminium activation.…”

Section: Synthesis Of Chiral Molecules Containing the Oxindole And In...mentioning

confidence: 99%

“…Therefore, the efficient construction of this scaffold has attracted a considerable amount of attention from the synthetic community. As a result, over the past several years, many elegant strategies have been established for the fast and efficient construction of indoloquinolizidine scaffold from simple starting materials . Inspired by these achievements, we developed a cascade reaction employing α-oxo-γ-butyrolactam 31 as a new N-containing pronucleophile for the synthesis of the butyrolactam-fused indoloquinolizidine scaffold (Scheme ) .…”

Section: Synthesis Of Chiral Molecules Containing the Oxindole And In...mentioning

confidence: 99%

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Asymmetric Catalytic Cascade Reactions for Constructing Diverse Scaffolds and Complex Molecules

Wang

2015

Acc. Chem. Res.

303

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With the increasing concerns about chemical pollution and sustainability of resources, among the significant challenges facing synthetic chemists are the development and application of elegant and efficient methods that enable the concise synthesis of natural products, drugs, and related compounds in a step-, atom- and redox-economic manner. One of the most effective ways to reach this goal is to implement reaction cascades that allow multiple bond-forming events to occur in a single vessel. This Account documents our progress on the rational design and strategic application of asymmetric catalytic cascade reactions in constructing diverse scaffolds and synthesizing complex chiral molecules. Our research is aimed at developing robust cascade reactions for the systematic synthesis of a range of interesting molecules that contain structural motifs prevalent in natural products, pharmaceuticals, and biological probes. The strategies employed to achieve this goal can be classified into three categories: bifunctional base/Brønsted acid catalysis, covalent aminocatalysis/N-heterocyclic carbene catalysis, and asymmetric organocatalytic relay cascades. By the use of rationally designed substrates with properly reactive sites, chiral oxindole, chroman, tetrahydroquinoline, tetrahydrothiophene, and cyclohexane scaffolds were successfully assembled under bifunctional base/Brønsted acid catalysis from simple and readily available substances such as imines and nitroolefins. We found that some of these reactions are highly efficient since catalyst loadings as low as 1 mol % can promote the multistep sequences affording complex architectures with high stereoselectivities and yields. Furthermore, one of the bifunctional base/Brønsted acid-catalyzed cascade reactions for the synthesis of chiral cyclohexanes has been used as a key step in the construction of the tetracyclic core of lycorine-type alkaloids and the formal synthesis of α-lycorane. Guided by the principles of covalent aminocatalysis and N-heterocyclic carbene catalysis, we synthesized chiral piperidine, indole, and cyclobutane derivatives. The synthesis of chiral cyclobutanes and pyrroloindolones showed unprecedented reactivity of substrates and catalysts. The development of the strategy of asymmetric organocatalytic relay cascades has provided a useful tool for the controlled synthesis of specific diastereomers in complex molecules. This Account gives a panoramic view and the logic of our research on the design, development, and applications of asymmetric catalytic cascade reactions that will potentially provide useful insights into exploring new reactions.

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“…As a result, over the past several years, many elegant strategies have been established for the fast and efficient construction of indoloquinolizidine scaffold from simple starting materials. 23 Inspired by these achievements, we . 24 Initially, Michael addition of 31 to 6 generated chiral hemiacetal 32 in the presence of secondary amine 33 through iminium activation.…”

Section: Accounts Of Chemical Researchmentioning

confidence: 96%

“…As a result, over the past several years, many elegant strategies have been established for the fast and efficient construction of indoloquinolizidine scaffold from simple starting materials. 23 Inspired by these achievements, we developed a cascade reaction employing α-oxo-γ-butyrolactam 31 as a new N-containing pronucleophile for the synthesis of the butyrolactam-fused indoloquinolizidine scaffold (Scheme 7). 24 Initially, Michael addition of 31 to 6 generated chiral hemiacetal 32 in the presence of secondary amine 33 through iminium activation.…”

Section: Synthesis Of Chiral Molecules Containing the Oxindole And In...mentioning

confidence: 99%

Section: Synthesis Of Chiral Molecules Containing the Oxindole And In...mentioning

confidence: 99%

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Asymmetric Catalytic Cascade Reactions for Constructing Diverse Scaffolds and Complex Molecules

Wang

2015

Acc. Chem. Res.

303

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“…Then, the double-Michael addition reaction occurs again to afford intermediate II . Subsequent intramolecular hemiaminalization affords the rigid 3-isoquinuclidone III after hydrolysis of the cyano group to an amide group. , This hydrolysis is probably why a mixed solvent of alcohol and water is required for the conversion from 1 and 2 to 3 , while water is not necessary for the conversion from 5 and 2 to 6 . Finally, the final bridged polycyclic lactam 3 is formed via hemiacetalation .…”

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confidence: 99%

Anion Cascade Reactions II: Synthesis of 3-Isoquinuclidone-Based Bridged Polycyclic Lactams

Shi,

Zhang,

Cao

et al. 2023

Org. Lett.

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A facile and convenient anion cascade strategy was developed for the synthesis of bridged-ring amides in moderate to excellent yields in one step in the presence of t BuOK in EtOH under mild conditions, starting from various cheap and commercially available 2-cyanoacetamides and precisely designed straight-chain and annular 1,4-dienones. This simple protocol was generally applicable to a wide range of substrates with high chemical conversion and diastereoselectivity.

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Double Stranded Helical Organo-lead 3D-Supramolecular Coordination Polymer Containing Copper Cyanide and Phenanthroline Ligand as Antimicrobial Agent

Etaiw

Abdou

2015

J Inorg Organomet Polym

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The supramolecular coordination polymer (SCP) [Cu(CN) 2 (Me 3 Pb)phen]; 1 is formed by selfassembly of K 3 [Cu(CN) 4 ], Me 3 PbCl and 1,10-phenanthroline (phen) ligand at ambient conditions. The copper center is coordinated to two ordered cyanide ligands and two nitrogen atoms of the phen ligand forming distorted tetrahedral configuration. The structure of 1 consists of repeating units of the tetrahedral Cu(phen)(CN) 2 fragments connected by the (Me 3 Pb) ? cations forming1-D helical chains. The 1-D helical chains are arranged in a unique way to construct a right-helical and a left-helical chain creating a double-helical 3-D network arranged in a unique AÁÁÁAÁÁÁA fashion. H-bonds and p-p stacking play an important role in stabilizing the structure of 1. IR, 1 H-NMR, electronic and luminescence spectra as well as thermal analysis are also investigated. The SCP 1 has high antimicrobial activity against E. coli and S. aureus and it also exhibits good activity against the fungal strains, C. albicans and A. Niger. The results of growth inhibiting effect indicated that the inhibitory effect is increased with an increase in concentration of the SCP 1.

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Progress in Asymmetric Organocatalyzed Michael Addition/Hemi-aminoacetalization/Acylimminium-Cyclization Cascade Reactions

Cited by 8 publications

References 4 publications

Asymmetric Catalytic Cascade Reactions for Constructing Diverse Scaffolds and Complex Molecules

Asymmetric Catalytic Cascade Reactions for Constructing Diverse Scaffolds and Complex Molecules

Anion Cascade Reactions II: Synthesis of 3-Isoquinuclidone-Based Bridged Polycyclic Lactams

Double Stranded Helical Organo-lead 3D-Supramolecular Coordination Polymer Containing Copper Cyanide and Phenanthroline Ligand as Antimicrobial Agent

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