Amines as key building blocks in Pd-assisted multicomponent processes

Bouyssi, Didier; Monteiro, Nuno; Balme, Geneviève

doi:10.3762/bjoc.7.163

Cited by 27 publications

(9 citation statements)

References 46 publications

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“…[2d, 6] Among them, gold(I)/(III) catalysis has played a major role [7] in generating chemical diversity/complexity under mild and selective conditions.…”

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confidence: 99%

One‐Pot Gold‐Catalyzed Synthesis of Azepino[1,2‐a]indoles

et al. 2012

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Als außergewöhnlich effektiver Katalysator für die Eintopfsynthese tricyclischer Azepinoindole in einer neuartigen Kaskadenreaktion erwies sich ein Komplex aus Gold(I) und einem N‐heterocyclischen Carben (IPr=1,3‐Di(isopropylphenyl)imidazol‐2‐yliden). Einfach verfügbare Substrate, hohe Chemoselektivität, gute Ausbeuten und Wasser als einziges stöchiometrisches Begleitprodukt sind einige der Hauptvorteile dieser Methode.

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“…[2d, 6] Among them, gold(I)/(III) catalysis has played a major role [7] in generating chemical diversity/complexity under mild and selective conditions.…”

mentioning

confidence: 99%

One‐Pot Gold‐Catalyzed Synthesis of Azepino[1,2‐a]indoles

et al. 2012

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“…A large number of N-containing saturated cyclic compounds are also elements employed to build molecular entities of medicinal interest. 50 Furthermore, N-containing saturated heterocyclic structures have found widespread clinical uses. 51 .…”

Section: Osmentioning

confidence: 99%

Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles

Kiss

Ouchakour

Nonn

et al. 2021

Synlett

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The current Account gives an insight into the synthesis of some N-heterocyclic β-amino acid derivatives and various functionalized saturated azaheterocycles accessed from substituted cycloalkenes via ring C=C bond oxidative cleavage followed by ring closing across double reductive amination. The ring-cleavage protocol has been accomplished according to two common approaches: a) Os-catalyzed dihydroxylation/NaIO4 vicinal diol oxidation and b) ozonolysis. A comparative study on these methodologies has been investigated. Due to the everincreasing relevance of organofluorine chemistry in drug research as well as of the high biological potential of β-amino acid derivatives several illustrative examples to the access of various fluorine-containing piperidine or azepane β-amino acid derivatives are also presented in the current Account.1 Introduction2 Olefin-Bond Transformation by Oxidative Ring Cleavage3 Synthesis of Saturated Azaheterocycles via Oxidative Ring-Opening/Ring-Closing Double Reductive Amination3.1 Importance of Fluorine-Containing Azaheterocycles in Pharmaceutical Research3.2 Synthesis of Azaheterocyclic Amino Acid Derivatives with a Piperidine or Azepane Framework through Oxidative Ring Opening/Reductive Amination3.2.1 Synthesis of Piperidine β-Amino Esters3.2.2 Synthesis of Azepane β-Amino Esters3.2.3 Synthesis of Fluorine-Containing Piperidine γ-Amino Esters3.3 Synthesis of Tetrahydroisoquinoline Derivatives through Oxidative Ring Opening/Reductive Amination Protocol3.4 Synthesis of Functionalized Benzazepines through Reductive Amination3.4.1 Synthesis of Benzo[c]azepines3.4.2 Synthesis of Benzo[d]azepines3.5 Synthesis of Various N-Heterocycles via Ozonolysis/Reductive Amination3.5.1 Synthesis of Compounds with an Azepane Ring3.5.2 Synthesis of Piperidine β-Amino Acids and Piperidine-Fused β-Lactams3.5.3 Synthesis of γ-Lactams with a Piperidine Ring3.5.4 Synthesis of other N-Heterocycles4 Summary and Outlook5 List of Abbreviations

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“…of HClO 4 in CH 2 Cl 2 /MeCN at room temperature. Under these acidic conditions, one diastereomer was cleanly and completely transformed into the other one (Scheme 104) [216].…”

Section: Introductionmentioning

confidence: 99%