Stereoselective Synthesis of 2-(2-Aminoalkyl)- and 1,3-Disubstituted Tetrahydro-1<i>H</i>-pyrido[4,3-<i>b</i>]- Benzofuran and Indole Derivatives

García-Muñoz, M. Jesús; Foubelo, Francisco; Yus, Miguel

doi:10.1021/acs.joc.6b01047

Cited by 28 publications

(7 citation statements)

References 44 publications

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“…Upon treatment with base, indolenine 3d underwent an intramolecular 1,2-addition to give the tricyclic cyclohexanone 16 in 85% yield. Meanwhile, the intermolecular 1,2-additions of indolenine 3b with lithium (trimethylsilyl)acetylide in the presence of BF 3 ·Et 2 O and propargyl bromide/In under sonication diastereoselectively installed the corresponding alkynyl and propargyl motifs, providing the indolines 17 and 18 both in >90% yield and >20:1 dr. Both of the obtained indolines could participate in a Pauson–Khand reaction to deliver the respective 6,5,5,5- and 6,5,6,5-tetracyclic compounds 19 and 20 with good control of diastereoselectivity.…”

Section: Results and Discussionmentioning

confidence: 99%

Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Substituted 1H-Indoles and Tryptophan Derivatives with Vinylcyclopropanes

et al. 2018

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Vinylcyclopropanes (VCPs) are known to generate 1,3-dipoles with a palladium catalyst that initially serve as nucleophiles to undergo [3 + 2] cycloadditions with electron-deficient olefins. In this report, we reverse this reactivity and drive the 1,3-dipoles to serve as electrophiles by employing 3-alkylated indoles as nucleophiles. This represents the first use of VCPs for the completely atom-economic functionalization of 3-substituted 1 H-indoles and tryptophan derivatives via a Pd-catalyzed asymmetric allylic alkylation (Pd-AAA). Excellent yields and high chemo-, regio-, and enantioselectivities have been realized, providing various indolenine and indoline products. The method is amenable to gram scale and works efficiently with tryptophan derivatives that contain a diketopiperazine or diketomorpholine ring, allowing us to synthesize mollenine A in a rapid and ligand-controlled fashion. The obtained indolenine products bear an imine, an internal olefin, and a malonate motif, giving multiple sites with diverse reactivities for product diversification. Complicated polycyclic skeletons can be conveniently constructed by leveraging this unique juxtaposition of functional groups.

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Section: Results and Discussionmentioning

confidence: 99%

Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Substituted 1H-Indoles and Tryptophan Derivatives with Vinylcyclopropanes

et al. 2018

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“…In the second case, an additional step, heating at 100 °C intermediates 242 , was necessary to get the final heterocycles (Scheme 103). [140] …”

Section: Organoindium Compoundsmentioning

confidence: 99%

Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

Foubelo

Yus

2020

The Chemical Record

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In this account the reactions of chiral N‐tert‐butylsulfinyl imines with organometallic reagents such as organoalkaline (lithium, sodium, potassium and cesium derivatives), organomagnesium, organozinc, organoboron, organoaluminium, organoindium and organosilicon compounds is comprehensively described. The reactivity in all cases is derived to synthetic applications in order to prepare interesting organic nitrogenated molecules, especially in the field of alkaloid compounds.

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“…The appealing skeletons and potential biological activities of tetrahydro-γ-carboline skeletons have received much attention among medicinal and synthetic chemists, and a number of approaches to chiral tetrahydro-γ-cabolines have been developed including the classical resolution 28 and diastereoselective iso -Pictet-Spengler cyclization reactions 29–31 . Catalytic asymmetric synthesis of enantiomerically enriched tetrahydro-γ-carbolines was also realized recently.…”

Section: Introductionmentioning

confidence: 99%

Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction

et al. 2019

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Enantiomerically enriched indole-containing heterocycles play a vital role in bioscience, medicine, and chemistry. As one of the most attractive subtypes of indole alkaloids, highly substituted tetrahydro-γ-carbolines are the basic structural unit in many natural products and pharmaceuticals. However, the syntheses of tetrahydro-γ-carbolines with high functionalities from readily available reagents are significant challenging. In particular, the stereodivergent syntheses of tetrahydro-γ-carbolines containing multi-stereogenic centers remain quite difficult. Herein, we report an expedient and stereodivergent assembly of tetrahydro-γ-carbolines with remarkably high levels of stereoselective control in an efficient cascade process from aldimine esters and indolyl allylic carbonates via a synergistic Cu/Ir catalyst system. Control experiments-guided optimization of synergistic catalysts and mechanistic investigations reveal that a stereodivergent allylation reaction and a subsequent highly stereoselective iso-Pictet-Spengler cyclization are the key elements to success.

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Stereoselective Synthesis of 2-(2-Aminoalkyl)- and 1,3-Disubstituted Tetrahydro-1H-pyrido[4,3-b]- Benzofuran and Indole Derivatives

Cited by 28 publications

References 44 publications

Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Substituted 1H-Indoles and Tryptophan Derivatives with Vinylcyclopropanes

Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Substituted 1H-Indoles and Tryptophan Derivatives with Vinylcyclopropanes

Chiral N‐tert‐Butylsulfinyl Imines: New Discoveries

Stereodivergent assembly of tetrahydro-γ-carbolines via synergistic catalytic asymmetric cascade reaction

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