Green asymmetric synthesis of tetrahydroquinolines in carbon dioxide medium promoted by lipophilic bifunctional tertiary amine – squaramide organocatalysts

Filatova, Evgeniya; Turova, O. V.; Nigmatov, A. G.; Zlotin, Sergei G.

doi:10.1016/j.tet.2017.11.057

Cited by 15 publications

(5 citation statements)

References 43 publications

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“…Among them, compounds 1109 and 1110 promoted the desired reaction at significantly lower pressure (75 bar) and temperature (35 °C) than previously known, less lipophilic catalysts (Figure 21). 466 Nitrostyrenes bearing a suitable amino or protected-amino group at the phenyl ortho position are also good substrates for the synthesis of tetrahydroquinolines by enantioselective organocatalytic domino reactions. Thus, Kim and Lee studied the reaction of 2-amino-β-nitrostyrenes 1111 with aldehydes 1112 in the presence of diphenylprolinol TMS ether 1115 to yield fully substituted chiral tetrahydroquinolines 1113 via an enamine Michael addition/hemiaminal formation domino process (Scheme 297).…”

Section: Synthesis Of 1234-tetrahydroquinolines Involving the Generat...mentioning

confidence: 99%

Progress in the Chemistry of Tetrahydroquinolines

2019

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Section: Synthesis Of 1234-tetrahydroquinolines Involving the Generat...mentioning

confidence: 99%

Progress in the Chemistry of Tetrahydroquinolines

2019

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“…Zlotin and co-workers showed the application of lipophilic squaramide catalyst bearing long hydrocarbon chain in asymmetric synthesis of all substituted tetrahydroquinoline derivatives. [38] Two catalysts O and P have been prepared containing eight and ten carbon alkoxy chain as the susbtituents which successfully triggered a double Michael cascade reaction between β-nitro styrene 2 and N-tosyl-2'-amino chalcones 76 leading to a facile access of the aza-cycles 94/94'. The reaction was performed in carbon dioxide medium at low pressure.…”

Section: Synthesis Of Azacyclesmentioning

confidence: 99%

Squaramide Catalyzed Asymmetric Synthesis of Five‐ and Six‐Membered Rings

Biswas¹,

Ghosh

Shankhdhar

et al. 2021

Asian J Org Chem

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Chiral analogues of squaramides have been fruitful in organocatalyzed asymmetric reactions over last decade. Alongside other H-bonding catalysts like ureas, thioureas: squaramides have been proved to be efficient asymmetric catalysts for the formation of acyclic and cyclic chiral molecules. A wide range of cyclic molecules bearing multiple functionalities and stereocenters have been synthesized by using several bifunctional squaramides as catalysts. These catalysts perform as base utilizing basic N atom in their chiral extension and help in stereoinduction by forming H-bonds with suitable H-bond acceptors. The present review focuses on assembling recent progresses of asymmetric synthesis of five and six membered rings promoted by squaramides. A handful of articles have been published by several research groups documenting asymmetric construction of five-and six-membered rings as part of interesting and complex molecular architectures. Different methodologies like conventional and formal cycloadditions or cascade reactions have been engineered through the assistance of chiral squaramides to fabricate the carbo-and heterocycles. This review also includes dual and cooperative catalytic system in which squaramide is one of the catalysts.

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“…The group of Zlotin then reported the same cascade reaction again in 2018 [17] . Compared with the previous reaction, new bifunctional squaramide catalysts modified by long‐chained alkoxy or polyfluoroalkoxy groups were used in this strategy.…”

Section: Catalytic Asymmetric Aza‐michael Addition Triggered Cascade Reactionsmentioning

confidence: 95%

Recent Advances in Catalytic Asymmetric Aza‐Michael Addition Triggered Cascade Reactions

Song

2021

Adv Synth Catal

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As an important branch of the Michael addition reaction, the aza‐Michael addition cascade reaction has been developed rapidly in recent years. This is because the reaction serves as an important method for effectively constructing functionalized C−N bonds, which can be widely used in the synthesis of chiral drugs and their intermediates and natural products. Given the importance of this topic, this review highlights the recent developments of aza‐Michael addition triggered cascade reactions in asymmetric synthesis, including aza‐Michael/Michael, aza‐Michael/Aldol, aza‐Michael/Henry, aza‐Michael/hemiacetal, aza‐Michael/Mannich, aza‐Michael/alkylation, aza‐Michael/cyclization, aza‐Michael/ring‐opening, aza‐Michael‐IED/HAD, aza‐Michael/INCR, and aza‐Michael/1,6‐conjugate addition reactions. In this paper, the reaction mechanism and derivatization experiments of different reactions are timely introduced to provide a more comprehensive theoretical basis for subsequent studies.

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Green asymmetric synthesis of tetrahydroquinolines in carbon dioxide medium promoted by lipophilic bifunctional tertiary amine – squaramide organocatalysts

Cited by 15 publications

References 43 publications

Progress in the Chemistry of Tetrahydroquinolines

Progress in the Chemistry of Tetrahydroquinolines

Squaramide Catalyzed Asymmetric Synthesis of Five‐ and Six‐Membered Rings

Recent Advances in Catalytic Asymmetric Aza‐Michael Addition Triggered Cascade Reactions

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