Screening chiral fluorinated binaphthyl ketone catalysts for asymmetric epoxidation

Stearman, Chad J.; Behar, Victor

doi:10.1016/s0040-4039(02)00173-9

Cited by 53 publications

(27 citation statements)

References 27 publications

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“…The biphenyl ketone 84 exhibited modest reactivity, but higher enantioselectivity relative to 83 in most cases. Better results were obtained with the chiral fluoro‐substituted binaphthyl ketone 85 (Scheme ) 172…”

Section: Reactions Via Covalent Transition Complexesmentioning

confidence: 99%

In the Golden Age of Organocatalysis

2004

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The term "organocatalysis" describes the acceleration of chemical reactions through the addition of a substoichiometric quantity of an organic compound. The interest in this field has increased spectacularly in the last few years as result of both the novelty of the concept and, more importantly, the fact that the efficiency and selectivity of many organocatalytic reactions meet the standards of established organic reactions. Organocatalytic reactions are becoming powerful tools in the construction of complex molecular skeletons. The diverse examples show that in recent years organocatalysis has developed within organic chemistry into its own subdiscipline, whose "Golden Age" has already dawned.

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Section: Reactions Via Covalent Transition Complexesmentioning

confidence: 99%

In the Golden Age of Organocatalysis

2004

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“…[79] Pertinent are the activating effects of a-fluoroketones, noted by Mello, Curci, and co-workers [80] that are a principal design feature of numerous epoxidation catalysts (Scheme 16). [81][82][83][84][85][86][87] The strongly electron-withdrawing properties of fluorine render the carbonyl carbon atom of a-fluoroketones highly electrophilic, hence these species readily form stable hydrates. Unsurprisingly, a-fluoroketones constitute some of the most efficient catalysts for the epoxidation of unactivated olefins when used in conjunction with oxone.…”

Section: A-fluoroketones For the Asymmetric Epoxidation Of Olefinsmentioning

confidence: 99%

Fluorine Conformational Effects in Organocatalysis: An Emerging Strategy for Molecular Design

2011

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Molecular design strategies that profit from the intrinsic stereoelectronic and electrostatic effects of fluorinated organic molecules have mainly been restricted to bio-organic chemistry. Indeed, many fluorine conformational effects remain academic curiosities with no immediate application. However, the renaissance of organocatalysis offers the possibility to exploit many of these well-described phenomena for molecular preorganization. In this minireview, we highlight examples of catalyst refinement by introduction of an aliphatic C-F bond which functions as a chemically inert steering group for conformational control.

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“…[79] Erwähnenswert sind die aktivierenden Effekte von a-Fluorketonen, die von Mello, Curci und Mitarbeitern beobachtet wurden; [80] dabei handelt es sich um ein wesentliches Designmerkmal zahlreicher Epoxidierungskatalysatoren (Schema 16). [81][82][83][84][85][86][87] Der stark elektronenziehende Fluorsubstituent macht das Carbonylkohlenstoffatom von a-Fluorketonen in hohem Maße elektrophil, und demzufolge bilden diese Spezies sehr Schema 13. Aminkatalysierte Oxidation von Alkenen.…”

Section: A-fluorketone Zur Asymmetrischen Epoxidierung Von Olefinenunclassified

“…Beispiele für fluorierte Ketone als Katalysatoren für die asymmetrische Epoxidierung. [81][82][83][84][85][86][87]…”

Section: A-fluorketone Zur Asymmetrischen Epoxidierung Von Olefinenunclassified

Konformative Fluoreffekte in der Organokatalyse: eine neuartige Strategie zum molekularen Design

2011

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Strategien zum molekularen Design, die von den intrinsischen stereoelektronischen und elektrostatischen Effekten fluorierter organischer Moleküle profitieren, sind bisher hauptsächlich auf die bioorganische Chemie beschränkt. Bei vielen konformativen Fluoreffekten handelt es sich zwar um akademische Kuriositäten ohne unmittelbare Anwendung, die Renaissance der Organokatalyse bietet allerdings die Möglichkeit zur Erforschung vieler dieser ausführlich beschriebenen Phänomene zur molekularen Präorganisation. In diesem Kurzaufsatz werden Beispiele zur Verbesserung von Katalysatoren durch die Einführung einer aliphatischen C‐F‐Bindung erläutert, die als eine chemisch inerte dirigierende Gruppe zur Steuerung der Konformation dient.

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Screening chiral fluorinated binaphthyl ketone catalysts for asymmetric epoxidation

Cited by 53 publications

References 27 publications

In the Golden Age of Organocatalysis

In the Golden Age of Organocatalysis

Fluorine Conformational Effects in Organocatalysis: An Emerging Strategy for Molecular Design

Konformative Fluoreffekte in der Organokatalyse: eine neuartige Strategie zum molekularen Design

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