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A Double Conformationally Restricted Dynamic Supramolecular System for the Substrate-Selective Epoxidation of Olefins-A Comparative Study on the Influence of Preorganization

Lindbäck, Emil LU ; Cherraben, Sawsen; Francoia, Jean-Patrick; Sheibani, Esmaeil LU ; Lukowski, Bartosz; Pron, Agnieszka; Norouzi Arasi, Hassan LU ; Mansson, Kristoffer; Bujalowski, Pawel and Cederbalk, Anna, et al. (2015) In ChemCatChem 7(2). p.333-348
Abstract
A double conformationally restricted kinetically labile supramolecular catalytic system, the third generation, was designed and synthesized. We investigated the substrate selectivity of this system by performing competitive pairwise epoxidations of pyridyl-and phenyl-appended olefins. We compared the obtained substrate selectivities to previous less preorganized generations of this system. Five different substrate pairs were investigated, and the present double conformationally restricted system showed higher normalized substrate selectivities ( pyridyl versus phenyl) for two of the substrate pairs than the previous less conformationally restricted generations. As for the preorganization of the components of the system, the catalyst, and... (More)
A double conformationally restricted kinetically labile supramolecular catalytic system, the third generation, was designed and synthesized. We investigated the substrate selectivity of this system by performing competitive pairwise epoxidations of pyridyl-and phenyl-appended olefins. We compared the obtained substrate selectivities to previous less preorganized generations of this system. Five different substrate pairs were investigated, and the present double conformationally restricted system showed higher normalized substrate selectivities ( pyridyl versus phenyl) for two of the substrate pairs than the previous less conformationally restricted generations. As for the preorganization of the components of the system, the catalyst, and the receptor part, it was shown that for each substrate pair there was one generation that was better than the other to generate substrate-selective catalysis. (Less)
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publication status
published
subject
keywords
epoxidation, supramolecular catalysis, hydrogen bonds, self-assembly, substrate selectivity
in
ChemCatChem
volume
7
issue
2
pages
333 - 348
publisher
John Wiley & Sons
external identifiers
  • wos:000347781400021
  • scopus:84920792286
ISSN
1867-3880
DOI
10.1002/cctc.201402726
language
English
LU publication?
yes
id
516424e4-5702-4022-b167-fe457d8a980e (old id 5069937)
date added to LUP
2015-02-25 14:58:40
date last changed
2017-01-01 04:17:18
@article{516424e4-5702-4022-b167-fe457d8a980e,
  abstract     = {A double conformationally restricted kinetically labile supramolecular catalytic system, the third generation, was designed and synthesized. We investigated the substrate selectivity of this system by performing competitive pairwise epoxidations of pyridyl-and phenyl-appended olefins. We compared the obtained substrate selectivities to previous less preorganized generations of this system. Five different substrate pairs were investigated, and the present double conformationally restricted system showed higher normalized substrate selectivities ( pyridyl versus phenyl) for two of the substrate pairs than the previous less conformationally restricted generations. As for the preorganization of the components of the system, the catalyst, and the receptor part, it was shown that for each substrate pair there was one generation that was better than the other to generate substrate-selective catalysis.},
  author       = {Lindbäck, Emil and Cherraben, Sawsen and Francoia, Jean-Patrick and Sheibani, Esmaeil and Lukowski, Bartosz and Pron, Agnieszka and Norouzi Arasi, Hassan and Mansson, Kristoffer and Bujalowski, Pawel and Cederbalk, Anna and Pham, Thanh Huong and Wixe, Torbjörn and Dawaigher, Sami and Wärnmark, Kenneth},
  issn         = {1867-3880},
  keyword      = {epoxidation,supramolecular catalysis,hydrogen bonds,self-assembly,substrate selectivity},
  language     = {eng},
  number       = {2},
  pages        = {333--348},
  publisher    = {John Wiley & Sons},
  series       = {ChemCatChem},
  title        = {A Double Conformationally Restricted Dynamic Supramolecular System for the Substrate-Selective Epoxidation of Olefins-A Comparative Study on the Influence of Preorganization},
  url          = {http://dx.doi.org/10.1002/cctc.201402726},
  volume       = {7},
  year         = {2015},
}