ChemInform Abstract: Proline‐Mediated Enantioselective Construction of Tetrahydropyridines via a Cascade Mannich‐Type/Intramolecular Cyclization Reaction.

Han, Rong-Gang; Wang, Yao; Li, Yuye; Xu, Peng‐Fei

doi:10.1002/chin.200843147

Cited by 2 publications

(3 citation statements)

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“…Most current procedures either require advanced starting materials or involve multistep and low-yielding reaction sequences. Among the more successful are a proline-mediated cascade Mannich-type/intramolecular cyclizations, a palladium-catalyzed alkynyl and allenyl iminium ion cyclizations, phosphine-promoted [3+3]-annulations of aziridines with allenoates, and radical cyclization of N -allylamino-substituted Baylis−Hillman adducts …”

Section: Introductionmentioning

confidence: 99%

Cerium Ammonium Nitrate-Catalyzed Multicomponent Reaction for Efficient Synthesis of Functionalized Tetrahydropyridines

2010

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A highly atom-economic one-pot synthesis of functionalized tetrahydropyridines by a multicomponent condensation reaction of β-keto ester, two equivalents of aromatic aldehyde, and two equivalents of amine in the presence of a catalytic amount of cerium ammonium nitrate (CAN) is reported. In this way, a series of pharmacologically interesting substituted piperidine derivatives were obtained in moderate to good yields at room temperature.

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Section: Introductionmentioning

confidence: 99%

Cerium Ammonium Nitrate-Catalyzed Multicomponent Reaction for Efficient Synthesis of Functionalized Tetrahydropyridines

2010

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“…28 On the basis of previous achievements in proline-catalyzed Mannich reactions, we developed a Mannich/intramolecular cyclization cascade reaction for the synthesis of chiral tetrahydropyridines from imines 43 and aqueous tetrahydro-2H-pyran-2,6-diol (Scheme 10). 29 The desired products were obtained in reasonable yields with excellent stereoselectivities. Later, we developed a relay catalytic three-component cascade reaction comprising aldehydes 45, nitroalkenes 3, and imines 46 for the efficient synthesis of fully substituted piperidines in the presence of two catalysts, (S)-5 and 48 (Scheme 11).…”

Section: Synthesis Of Chiral Molecules Containing the Tetrahydropyridmentioning

confidence: 98%

“…Furthermore, they have also been used as fundamental building blocks in various transformations . On the basis of previous achievements in proline-catalyzed Mannich reactions, we developed a Mannich/intramolecular cyclization cascade reaction for the synthesis of chiral tetrahydropyridines from imines 43 and aqueous tetrahydro-2 H -pyran-2,6-diol (Scheme ) . The desired products were obtained in reasonable yields with excellent stereoselectivities.…”

Section: Synthesis Of Chiral Molecules Containing the Tetrahydropyrid...mentioning

confidence: 99%

Asymmetric Catalytic Cascade Reactions for Constructing Diverse Scaffolds and Complex Molecules

Wang

2015

Acc. Chem. Res.

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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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ChemInform Abstract: Proline‐Mediated Enantioselective Construction of Tetrahydropyridines via a Cascade Mannich‐Type/Intramolecular Cyclization Reaction.

Cited by 2 publications

References 1 publication

Cerium Ammonium Nitrate-Catalyzed Multicomponent Reaction for Efficient Synthesis of Functionalized Tetrahydropyridines

Cerium Ammonium Nitrate-Catalyzed Multicomponent Reaction for Efficient Synthesis of Functionalized Tetrahydropyridines

Asymmetric Catalytic Cascade Reactions for Constructing Diverse Scaffolds and Complex Molecules

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