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A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger’s Base

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posted on 18.12.2015, 00:00 by Sami Dawaigher, Kristoffer Månsson, Erhad Ascic, Josep Artacho, Roger Mårtensson, Nagarajan Loganathan, Ola F. Wendt, Michael Harmata, Victor Snieckus, Kenneth Wärnmark
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.