Tröger's Base Twisted Amides: Endo Functionalization and Synthesis of an Inverted Crown Ether
(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:
https://lup.lub.lu.se/record/3124167
- author
- 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
- organization
- publishing date
- 2012
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Organic Letters
- volume
- 14
- issue
- 18
- pages
- 4706 - 4709
- publisher
- The American Chemical Society (ACS)
- external identifiers
-
- wos:000308958500002
- pmid:22958089
- scopus:84868235354
- pmid:22958089
- 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
- 2016-04-01 11:04:43
- date last changed
- 2022-01-26 05:10:48
@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 (ACS)}}, 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}}, doi = {{10.1021/ol302022y}}, volume = {{14}}, year = {{2012}}, }