An intramolecular, Ni(0)-mediated approach to the nonracemic biaryl portion of vancomycin

Lipshutz, Bruce H.; Müller, Peter; Leinweber, Dirk

doi:10.1016/s0040-4039(99)00557-2

Cited by 23 publications

(12 citation statements)

References 15 publications

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“…This strategy has found application in the (partial) synthesis of natural products (and derivatives)92–96 and ligands for catalytic asymmetric synthesis;97–100 some examples are shown in Scheme . Lipshutz et al synthesized ( P )‐ 66 ,92 a model system for the AB system of vancomycin ( 1 , Figure 1), and O ‐permethyltellimagrandin II (( P )‐ 67 ),96 a member of the ellagitannin family. The natural product kotanin (( P )‐ 69 ) was constructed by Lin and co‐workers 93.…”

Section: Biaryls By Asymmetric Cc Couplingmentioning

confidence: 99%

Atroposelective Synthesis of Axially Chiral Biaryl Compounds

et al. 2005

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A rotationally hindered and thus stereogenic biaryl axis is the structurally and stereochemically decisive element of a steadily growing number of natural products, chiral auxiliaries, and catalysts. Thus, it is not surprising that significant advances have been made in the asymmetric synthesis of axially chiral biaryl compounds over the past decade. In addition to the classic approach (direct stereoselective aryl-aryl coupling), innovative concepts have been developed in which the asymmetric information is introduced into a preformed, but achiral-that is, symmetric or configurationally labile-biaryl compound, or in which an aryl--C single bond is stereoselectively transformed into an axis. This Review classifies these strategies according to their underlying concepts and critically evaluates their scope and limitations with reference to selected model reactions and applications. Furthermore, the preconditions required for the existence of axial chirality in biaryl compounds are discussed.

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Section: Biaryls By Asymmetric Cc Couplingmentioning

confidence: 99%

Atroposelective Synthesis of Axially Chiral Biaryl Compounds

et al. 2005

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“…Diese Strategie fand Anwendung in der Synthese von Naturstoffen (und Derivaten) [92][93][94][95][96] und von Liganden für die katalytische asymmetrische Synthese; [97][98][99][100] einige Beispiele hierfür sind in Schema 5 gezeigt. Lipshutz et al synthetisierten (P)-66, [92] ein Modell für das AB-System von Vancomycin (1, Abbildung 1), und O-Permethyltellimagrandin II ((P)-67), [96] ein Ellagitannin, während der Naturstoff Kotanin ((P)-69) von Lins Gruppe aufgebaut wurde.…”

Section: Biaryle Durch Asymmetrische C-c-kupplungunclassified

“…Lipshutz et al synthetisierten (P)-66, [92] ein Modell für das AB-System von Vancomycin (1, Abbildung 1), und O-Permethyltellimagrandin II ((P)-67), [96] ein Ellagitannin, während der Naturstoff Kotanin ((P)-69) von Lins Gruppe aufgebaut wurde. [93,94] Die enantiomerenreinen Diphosphane (P)-70 und (M)-71, die sich als chirale Liganden in katalytischen asymmetrischen Hydrierungen einsetzen lassen, wurden von GenÞt, Marinetti und Mitarbeitern [97,98] bzw.…”

Section: Biaryle Durch Asymmetrische C-c-kupplungunclassified

Atropselektive Synthese axial‐chiraler Biaryle

et al. 2005

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Eine rotationsgehinderte und dadurch stereogene Biarylachse ist das strukturell und stereochemisch entscheidende Element einer ständig wachsenden Zahl von Naturstoffen, chiralen Auxiliaren und Katalysatoren. Daher ist es nicht überraschend, dass im letzten Jahrzehnt bedeutende Fortschritte in der asymmetrischen Synthese axial‐chiraler Biaryle erzielt worden sind. Neben dem klassischen Zugangsweg, der direkten Aryl‐Aryl‐Kupplung, sind innovative Konzepte entwickelt worden, in denen die asymmetrische Information in ein schon vorhandenes, aber nicht optisch aktives – symmetrisches oder konfigurativ labiles – Biaryl eingeführt oder eine Aryl‐C‐Einfachbindung stereoselektiv in eine Achse umgewandelt wird. In diesem Aufsatz werden die Strategien nach den zugrunde liegenden Konzepten klassifiziert, und ihre Anwendungsbreite und ihre Beschränkungen werden anhand ausgewählter Beispiele kritisch beurteilt. Ferner werden die Voraussetzungen für das Auftreten von Axialchiralität diskutiert.

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“…13 The attempted Ullmann-like reductive coupling of 4 (R = Br) with copper(I) thiophene-2-carboxylate (CuTC) 14 did not give any significant conversion at ambient temperature, while at 80°C complete hydrodehalogenation was observed (method E). Finally successful was the nickel(0)-mediated coupling 15 of 4 (X = I) under the conditions developed by Lipshutz et al: 16 the desired constitutionally unsymmetric biaryl lactone 2 was obtained as the only product, in a quite satisfactory yield of 45% (method F). 17 In the 1 H NMR spectrum, the methylene group of the lactone 2 appeared as an AB system due to the diastereotopic nature of the two protons, indicating that -in contrast to the rapidly enantiomerizing 6-membered analogs 6 -the 7membered lactone 2 is configurationally stable at room temperature, at least within the NMR time scale.…”

Section: )mentioning

confidence: 99%

Synthesis of Constitutionally Unsymmetric 7-Membered Biaryl Lactones by Ni-Mediated Intramolecular Coupling

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An intramolecular, Ni(0)-mediated approach to the nonracemic biaryl portion of vancomycin

Cited by 23 publications

References 15 publications

Atroposelective Synthesis of Axially Chiral Biaryl Compounds

Atroposelective Synthesis of Axially Chiral Biaryl Compounds

Atropselektive Synthese axial‐chiraler Biaryle

Synthesis of Constitutionally Unsymmetric 7-Membered Biaryl Lactones by Ni-Mediated Intramolecular Coupling

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