Enantioselective Organocatalytic Amine Conjugate Addition

Chen, Young K.; Yoshida, Masanori; MacMillan, David W. C.

doi:10.1021/ja063267s

Cited by 290 publications

(130 citation statements)

References 12 publications

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“…[173] Wie bei den asymmetrischen Friedel-Crafts-Reaktionen ist die erhöhte Elektrophile auch für zahlreiche Lewis-Basekatalysierte Michael-Additionen von großer Bedeutung. Der Angriff von Malonaten, [174] Cumarinen, [175] Nitroalkanen, [176] Siloxyfuranen, [177] Sulfiden [178] und Aminen [179] auf chirale Iminiumionen ergibt hohe Enantioselektivitäten [Gl. (2) in Schema 41].…”

Section: Phosphankatalysierte Cycloadditionenunclassified

Lewis‐Base‐Katalyse in der organischen Synthese

2008

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Das Erbe von Gilbert Newton Lewis (1875–1946) ist im Wörterbuch der chemischen Bindung und Reaktivität allgegenwärtig. Die Bedeutung seines Konzepts der Donor‐Akzeptor‐Bindung kommt in den eponymen Grundbegriffen für Elektronenpaarakzeptoren (Lewis‐Säuren) und ‐donoren (Lewis‐Basen) zum Ausdruck. Lewis erkannte, dass Säuren nicht automatisch Wasserstoff enthalten müssen (Brønsted‐Säuren) und trug so zum Sturz des “modernen Protonenkults” bei. Seine Entdeckung läutete zunächst die Entwicklung von Lewis‐Säuren als Reagentien und Katalysatoren für organische Reaktionen ein, in den letzten Jahren wurde aber offensichtlich, dass für diese Zwecke auch Lewis‐Basen eingesetzt werden können. Bezüglich der Beschleunigung chemischer Reaktionen ergänzen Lewis‐Basen die entsprechenden Lewis‐Säuren nicht nur elektronisch: Tatsächlich können Lewis‐Basen die Elektrophilie wie auch die Nucleophilie der Verbindungen verstärken, an die sie gebunden werden. Diese unterschiedliche Reaktivität resultiert in einer bemerkenswerten Vielfalt Lewis‐Base‐katalysierter Reaktionen.

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Section: Phosphankatalysierte Cycloadditionenunclassified

Lewis‐Base‐Katalyse in der organischen Synthese

2008

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“…21 We hypothesized that enaminone 2.66 might be readily synthesized from aldehyde 2.70 by means of our previous strategy and that the hydroxy group of 2.67 might be cleaved in a reductive fashion to provide enaminone 2.66. With the aid of an imidazolidinone catalyst, protected hydroxylamine 2.71 underwent Michael addition to aldehyde 2.72 to give amino aldehyde 2.70 with excellent enantioselectivity (Scheme 16).…”

Section: Scheme 15 Retrosynthetic Plan To Obtain Enantiomerically-enrmentioning

confidence: 99%

2,3-Dihydropyridin-4(1H)-ones and 3-Aminocyclohex-2-enones: Synthesis, Functionalization, and Applications to Alkaloid Synthesis

Seki¹,

Georg²

2014

Synlett

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This account summarizes our recent investigations into the chemistry of 2,3-dihydropyridin-4(1H)-ones and 3-aminocyclohex-2-enones (enaminones). These enaminones are exceptionally versatile chemical scaffolds that serve as valuable intermediates in the synthesis of indolizidine and quinolizidine alkaloids and other bioactive compounds. Since we reported our first method for constructing enaminones in 2006, we have developed a number of additional approaches to the synthesis and derivatization of enaminones and we have explored their applications in natural product synthesis.

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“…[57] This challenging approach required the identification of an amine that functioned as a nucleophile in a 1,4-addition without activating the iminium ion (racemic pathway). At the same time, a second amine needed to be found that performed as an iminium catalyst and not as a nucleophile (consumption of the catalyst).…”

Section: Discovery Of New Substrate Combinationsmentioning

confidence: 99%

Asymmetric Organocatalysis: From Infancy to Adolescence

2008

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After an initial period of validating asymmetric organocatalysis by using a wide range of important model reactions that constitute the essential tools of organic synthesis, the time has now been reached when organocatalysis can be used to address specific issues and solve pending problems of stereochemical relevance. This Review deals with selected studies reported in 2006 and the first half of 2007, and is intended to highlight four main aspects that may be taken as testimony of the present status and prospective of organocatalysis: a) chemical efficiency; b) discovery of new substrate combinations to give new asymmetric syntheses; c) development of new catalysts for specific purposes by using mechanistic findings; and d) applications of organocatalytic reactions in the asymmetric total synthesis of target natural products and known compounds of biological and pharmaceutical relevance.

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Enantioselective Organocatalytic Amine Conjugate Addition

Cited by 290 publications

References 12 publications

Lewis‐Base‐Katalyse in der organischen Synthese

Lewis‐Base‐Katalyse in der organischen Synthese

2,3-Dihydropyridin-4(1H)-ones and 3-Aminocyclohex-2-enones: Synthesis, Functionalization, and Applications to Alkaloid Synthesis

Asymmetric Organocatalysis: From Infancy to Adolescence

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