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Contra‐Thermodynamic, Photocatalytic E→Z Isomerization of Styrenyl Boron Species: Vectors to Facilitate Exploration of Two‐Dimensional Chemical Space

Molloy, John J. ; Metternich, Jan B. ; Daniliuc, Constantin G. ; Watson, Allan J. B. ; Gilmour, Ryan

Angewandte Chemie (International ed.), 2018-03, Vol.57 (12), p.3168-3172 [Periódico revisado por pares]

Germany: Wiley Subscription Services, Inc

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  • Título:
    Contra‐Thermodynamic, Photocatalytic E→Z Isomerization of Styrenyl Boron Species: Vectors to Facilitate Exploration of Two‐Dimensional Chemical Space
  • Autor: Molloy, John J. ; Metternich, Jan B. ; Daniliuc, Constantin G. ; Watson, Allan J. B. ; Gilmour, Ryan
  • Assuntos: Alkenes ; Boron ; conformational analysis ; Isomerization ; isomerizations ; Isomers ; natural products ; Photocatalysis ; Polarity ; Substitutes
  • É parte de: Angewandte Chemie (International ed.), 2018-03, Vol.57 (12), p.3168-3172
  • Notas: These authors contributed equally to this work.
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  • Descrição: Designing strategies to access stereodefined olefinic organoboron species is an important synthetic challenge. Despite significant advances, there is a striking paucity of routes to Z‐α‐substituted styrenyl organoborons. Herein, this strategic imbalance is redressed by exploiting the polarity of the C(sp2)−B bond to activate the neighboring π system, thus enabling a mild, traceless photocatalytic isomerization of readily accessible E‐α‐substituted styrenyl BPins to generate the corresponding Z‐isomers with high fidelity. Preliminary validation of this contra‐thermodynamic E→Z isomerization is demonstrated in a series of stereoretentive transformations to generate Z‐configured trisubstituted alkenes, as well as in a concise synthesis of the anti‐tumor agent Combretastatin A4. It's EZ: Exploitation of the polarity of the C(sp2)−B bond to activate the neighboring π system enables a mild, traceless photocatalytic isomerization of readily accessible E‐α‐substituted styrenyl BPins to generate the corresponding Z‐isomers with high fidelity. The method is used for a series of stereoretentive transformations to generate Z‐configured trisubstituted alkenes, as well as in a concise synthesis of the anti‐tumor agent combretastatin A4.
  • Editor: Germany: Wiley Subscription Services, Inc
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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