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

作者：Dawaigher Sami; Mansson Kristoffer; Ascic Erhad; Artacho Josep; Martensson Roger; Loganathan Nagarajan; Wendt Ola F; Harmata Michael^*; Snieckus Victor; Waernmark Kenneth

来源：Journal of Organic Chemistry, 2015, 80(24): 12006-12014.

DOI：10.1021/acs.joc.5b01921

An efficient protocol has been developed for the exo-mono and exo,exo-bis functionalization of Troger's base in the benzylic 6 and 12 positions of the diazocine ring. The lithiation of Troger's base using s-BuLi/TMEDA followed by electrophilic quench affords exo-mono- and exo,exo-bis-substituted derivatives of Troger'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.

• 出版日期2015-12-18