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

Summary, in English

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.

• Author: Sami Dawaigher; Kristoffer Månsson; Erhad Ascic; Josep Artacho Ruiz; Roger Mårtensson; Nagarajan Loganathan; Ola Wendt; Michael Harmata; Victor Snieckus; Kenneth Wärnmark
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2015
• Language: English
• Pages: 12006-12014
• Publication/Series: Journal of Organic Chemistry
• Volume: 80
• Issue: 24
• Links: http://dx.doi.org/10.1021/acs.joc.5b01921
• Document type: Journal article
• Publisher: The American Chemical Society (ACS)
• Topic: Organic Chemistry
• Status: Published
• ISBN/ISSN/Other: ISSN: 1520-6904