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A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger's Base.
Dawaigher, Sami; Månsson, Kristoffer; Ascic, Erhad; Artacho, Josep; Mårtensson, Roger; Loganathan, Nagarajan; Wendt, Ola F; Harmata, Michael; Snieckus, Victor; Wärnmark, Kenneth.
Afiliação
  • Dawaigher S; Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
  • Månsson K; Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
  • Ascic E; Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
  • Artacho J; Department of Chemistry, Queen's University , Kingston, ON K7L 3N6, Canada.
  • Mårtensson R; Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
  • Loganathan N; Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
  • Wendt OF; Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
  • Harmata M; Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
  • Snieckus V; Department of Chemistry, University of Missouri-Columbia , Columbia, Missouri 65211, United States.
  • Wärnmark K; Department of Chemistry, Queen's University , Kingston, ON K7L 3N6, Canada.
J Org Chem ; 80(24): 12006-14, 2015 Dec 18.
Article em En | MEDLINE | ID: mdl-26597045
ABSTRACT
An efficient protocol has been developed for the exo-mono and exo,exo-bis functionalization of Tröger's base in the benzylic 6 and 12 positions of the diazocine ring. The lithiation of Tröger's base using s-BuLi/TMEDA followed by electrophilic quench affords exo-mono- and exo,exo-bis-substituted derivatives of Tröger's base in good to excellent yields. The variation of the number of equivalents of s-BuLi/TMEDA and the order of addition of the electrophile strongly govern the outcome of the reaction for each electrophile.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2015 Tipo de documento: Article País de afiliação: Suécia
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2015 Tipo de documento: Article País de afiliação: Suécia