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Tröger's Base Twisted Amides: Endo Functionalization and Synthesis of an Inverted Crown Ether

Artacho Ruiz, Josep LU ; Ascic, Erhad; Rantanen, Toni; Wallentin, Carl-Johan LU ; Dawaigher, Sami LU ; Bergquist, Karl-Erik LU ; Harmata, Michael; Snieckus, Victor and Wärnmark, Kenneth LU (2012) In Organic Letters 14(18). p.4706-4709
Abstract
Taking advantage of the unconventional reactivity of twisted mono- and bis-amides of Tröger's base (TB), rac-6 and rac-7, respectively, the first synthesis of a 6-endo-monosubstituted TB analogue, rac-9, and the first rational synthesis of a 6,12-endo,endo-disubstituted TB analogue, rac-11, have been achieved. The bis-TB crown ether, meso-13, was prepared starting from rac-7. Meso-13 constitutes a rare example of a crown ether with an inverted methylene bridge-to-bridge bis-TB conformation both in solution and in the solid state, resulting in a reluctance to act as a receptor for cations.
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic Letters
volume
14
issue
18
pages
4706 - 4709
publisher
The American Chemical Society
external identifiers
  • wos:000308958500002
  • pmid:22958089
  • scopus:84868235354
ISSN
1523-7052
DOI
10.1021/ol302022y
language
English
LU publication?
yes
id
e3de1707-9003-4694-a239-a50f57c8df51 (old id 3124167)
date added to LUP
2012-10-09 16:09:28
date last changed
2017-10-22 03:28:38
@article{e3de1707-9003-4694-a239-a50f57c8df51,
  abstract     = {Taking advantage of the unconventional reactivity of twisted mono- and bis-amides of Tröger's base (TB), rac-6 and rac-7, respectively, the first synthesis of a 6-endo-monosubstituted TB analogue, rac-9, and the first rational synthesis of a 6,12-endo,endo-disubstituted TB analogue, rac-11, have been achieved. The bis-TB crown ether, meso-13, was prepared starting from rac-7. Meso-13 constitutes a rare example of a crown ether with an inverted methylene bridge-to-bridge bis-TB conformation both in solution and in the solid state, resulting in a reluctance to act as a receptor for cations.},
  author       = {Artacho Ruiz, Josep and Ascic, Erhad and Rantanen, Toni and Wallentin, Carl-Johan and Dawaigher, Sami and Bergquist, Karl-Erik and Harmata, Michael and Snieckus, Victor and Wärnmark, Kenneth},
  issn         = {1523-7052},
  language     = {eng},
  number       = {18},
  pages        = {4706--4709},
  publisher    = {The American Chemical Society},
  series       = {Organic Letters},
  title        = {Tröger's Base Twisted Amides: Endo Functionalization and Synthesis of an Inverted Crown Ether},
  url          = {http://dx.doi.org/10.1021/ol302022y},
  volume       = {14},
  year         = {2012},
}