A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger's Base.
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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MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2015
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Article
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Suécia