Control over Stereogenic N–N Axes by Pd-Catalyzed 5-endo-Hydroaminocyclizations

Hutskalova, Valeriia; Sparr, Christof

doi:10.1055/a-1993-6899

Cited by 21 publications

(21 citation statements)

References 39 publications

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“…Under mild conditions, a wide range of N−N‐linked bisindoles 125 were prepared with up to 90 % yield and 74 % ee (Scheme 39). [66] …”

Section: Asymmetric Cyclization Synthesis Of Heterobiarylsmentioning

confidence: 99%

“…Under mild conditions, a wide range of NÀ N-linked bisindoles 125 were prepared with up to 90 % yield and 74 % ee (Scheme 39). [66] In 2023, Shi, Zhang, and co-workers performed CPAcatalyzed enantioselective [2 + 3] cycloaddition of 2,3-diketoesters 87 and indole-based enaminones 126 (Scheme 40). [67] A wide range of axially chiral N,N'-bisindoles and N,N'-pyrrolylindoles 127 were synthesized in excellent enantioselectivities (up to 98 % ee) via de novo indole-ring formation process involving two nucleophilic addition (Int-73 to Int-75), two dehydration (Int-75 to Int-77), aromatization, and isomerization.…”

Section: Intermolecular Cyclizationmentioning

confidence: 99%

“…Atroposelective synthesis of NÀ N bisindole via Pd-catalyzed intramolecular reaction. [66] Scheme 40. Atroposelective synthesis of NÀ N bisindole via de novo indolering formation.…”

Section: Intermolecular Cyclizationmentioning

confidence: 99%

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Atroposelective Synthesis of Heterobiaryls through Ring Formation

Sun

Sharif

Chen

et al. 2023

Chemistry A European J

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Atropisomeric heterobiaryls play a vital role in natural products, chiral ligands, organocatalysts, and other research fields, which have aroused great interest from chemists in recent years. Until now, a growing number of optically active heterobiaryls based on indole, quinoline, isoquinoline, pyridine, pyrrole, azole, and benzofuran skeletons have been successfully synthesized through metal or organic catalytic cross-coupling, functionalization of prochiral or racemic heterobiaryls, and ring formation. Among different strategies for the atroposelective synthesis of heterobiaryls, the strategy of ring formation has become a vital tool toward this goal. In this review, we summarize the enantioselective synthesis of axially chiral heterobiaryls through ring formation approaches, such as cycloaddition, cyclization, and chirality conversion. Meanwhile, the reaction mechanism and the corresponding applications of the chiral heterobiaryls are also discussed.[a] H.

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“…Under mild conditions, a wide range of N−N‐linked bisindoles 125 were prepared with up to 90 % yield and 74 % ee (Scheme 39). [66] …”

Section: Asymmetric Cyclization Synthesis Of Heterobiarylsmentioning

confidence: 99%

Section: Intermolecular Cyclizationmentioning

confidence: 99%

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Atroposelective Synthesis of Heterobiaryls through Ring Formation

Sun

Sharif

Chen

et al. 2023

Chemistry A European J

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“…Inspired by the synthesis of atropisomeric indoles by Kitagawa, [35] the group of Sparr reported the synthesis of bisindoles through the atroposelective Pd catalyzed intramolecular 5-endo-hydroamino-cyclization of N-(2-phenyethynyl)amino carbazoles. [36] After a comprehensive optimization of the reaction conditions (transition metals, ligands, solvent and additives), the best results were obtained when Pd(CH 3 CN)Cl 2 was combined with (R)-DM-SEGPHOS ligand and the reaction performed in ethanol at 60 °C for 66 hours. Nevertheless, the process revealed some limits showing in general moderate yields and enantioselectivities (Scheme 19).…”

Section: Synthesis Of Nà N Axially Chiral Indolyl-carbazoles By Pd Ca...mentioning

confidence: 99%

Enantioselective Strategies for The Synthesis of N−N Atropisomers

et al. 2023

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Axially chiral compounds have been always considered a laboratory curiosity with rare prospects of being applied in asymmetric synthesis. Things have changed very quickly in the last twenty years when it was understood the important role and the enormous impact that these compounds have in medicinal, biological and material chemistry. The asymmetric synthesis of atropisomers became a rapidly expanding field and recent reports on the development of N−N atropisomers strongly prove how this research field is a hot topic open to new challenges and frontiers of asymmetric synthesis. This review focuses on the recent advances in the enantioselective synthesis of N−N atropisomers highlighting the strategies and breakthroughs to obtain this novel and stimulating atropisomeric framework.

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“…The identification of the cooperative catalysis of chiral phosphoric acid and InBr 3 was key for the high efficiency and enantioselectivity of this catalytic system. Notably during the preparation of this manuscript, two alternative and elegant Pd-catalyzed atroposelective indolization methods for the construction of N–N linked bisindoles were reported by the Liu group and the Sparr group, respectively. , Successful access to these novel compounds will surely open new avenues for the development of asymmetric catalytic method development.…”

mentioning

confidence: 99%

Chiral Acid-Catalyzed Atroposelective Indolization Enables Access to 1,1′-Indole-Pyrroles and Bisindoles Bearing a Chiral N–N Axis

et al. 2023

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We present herein a highly atroposelective indolization for the efficient synthesis of 1,1′-biheteroaryls bearing a chiral N–N axis. Under the cooperative catalysis of chiral phosphoric acid and InBr3, the reactions between 2,3-diketoesters and 1,3-dione-derived enamines resulted in a highly enantioselective construction of 1,1′-pyrrole-indoles with up to 92% yield, 94% enantiomeric excess (ee), or bisindoles in up to 92% ee. Derivatizations of these compounds to diverse functionalized N–N linked axially chiral biheteroaryls have also been demonstrated.

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Control over Stereogenic N–N Axes by Pd-Catalyzed 5-endo-Hydroaminocyclizations

Cited by 21 publications

References 39 publications

Atroposelective Synthesis of Heterobiaryls through Ring Formation

Atroposelective Synthesis of Heterobiaryls through Ring Formation

Enantioselective Strategies for The Synthesis of N−N Atropisomers

Chiral Acid-Catalyzed Atroposelective Indolization Enables Access to 1,1′-Indole-Pyrroles and Bisindoles Bearing a Chiral N–N Axis

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