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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 LU ; Månsson, Kristoffer; Ascic, Erhad; Artacho Ruiz, Josep LU ; Mårtensson, Roger; Loganathan, Nagarajan LU ; Wendt, Ola LU ; Harmata, Michael; Snieckus, Victor and Wärnmark, Kenneth LU (2015) In Journal of Organic Chemistry 80(24). p.12006-12014
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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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
80
issue
24
pages
12006 - 12014
publisher
The American Chemical Society
external identifiers
  • pmid:26597045
  • wos:000366877900013
  • scopus:84952802727
ISSN
1520-6904
DOI
10.1021/acs.joc.5b01921
language
English
LU publication?
yes
id
cd8979ee-25b5-4293-9952-9077bd2e1bf5 (old id 8234827)
date added to LUP
2015-12-16 17:34:47
date last changed
2017-07-09 03:20:00
@article{cd8979ee-25b5-4293-9952-9077bd2e1bf5,
  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.},
  author       = {Dawaigher, Sami and Månsson, Kristoffer and Ascic, Erhad and Artacho Ruiz, Josep and Mårtensson, Roger and Loganathan, Nagarajan and Wendt, Ola and Harmata, Michael and Snieckus, Victor and Wärnmark, Kenneth},
  issn         = {1520-6904},
  language     = {eng},
  number       = {24},
  pages        = {12006--12014},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger's Base.},
  url          = {http://dx.doi.org/10.1021/acs.joc.5b01921},
  volume       = {80},
  year         = {2015},
}