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Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)‐Verapamil

Oliveira, Caio C. ; Pfaltz, Andreas ; Correia, Carlos Roque Duarte

Angewandte Chemie, 2015-11, Vol.127 (47), p.14242-14245 [Periódico revisado por pares]

Weinheim: WILEY‐VCH Verlag

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  • Título:
    Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)‐Verapamil
  • Autor: Oliveira, Caio C. ; Pfaltz, Andreas ; Correia, Carlos Roque Duarte
  • Assuntos: Alkenes ; Blocking ; Branched ; Calcium ; Calcium channel blockers ; Calcium channels ; Channels ; Chemistry ; Enantiomers ; Heck‐Reaktion ; Lactones ; N,N‐Liganden ; Olefins ; Palladium ; Quartäre Stereozentren ; Salts ; Synthesis ; Verapamil
  • É parte de: Angewandte Chemie, 2015-11, Vol.127 (47), p.14242-14245
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
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  • Descrição: We describe herein a highly regio‐ and enantioselective Pd‐catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all‐carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine‐ and pyrazino‐oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to >99:1. Both linear and branched substituents on the olefins were well‐tolerated. The potential of this new method is demonstrated by the straightforward synthesis of several O‐methyl lactols and lactones containing quaternary stereocenters, together with a concise enantioselective total synthesis of the calcium channel blocker verapamil. Maßgeschneiderte chirale N,N‐Liganden und Aryldiazoniumsalze ermöglichen die enantioselektive Einführung ausschließlich kohlenstoffsubstituierter quartärer Stereozentren durch eine Heck‐Reacktion mit acyclischen Olefinen. Die Methode führt zu komplexen Molekülgerüsten, was eine kurze Totalsynthese von (R)‐Verapamil belegt.
  • Editor: Weinheim: WILEY‐VCH Verlag
  • Idioma: Inglês;Alemão
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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