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Conformationally restricted dynamic supramolecular catalysts for substrate-selective epoxidations.

Sheibani, Esmaeil LU and Wärnmark, Kenneth LU (2012) In Organic and Biomolecular Chemistry 10(10). p.2059-2067
Abstract
A second generation of a substrate-selective dynamic supramolecular catalytic system consisting of a catalyst part and a receptor part, connected by a hydrogen-bonding motif, has been realized based on rational design. The results from analyses of the equilibrium mixture of the species generated by the components of the first generation system led us to selectively lock the cisoid conformation of the catalyst part to increase the amount of the substrate-selective catalytic cavity in the equilibrium mixture. This was realized by strapping the catalyst part by organic synthesis. This strapping led to an increase in substrate selectivity in the pair-wise competitive epoxidations of pyridyl- vs. phenyl-appended styrenes and pyridyl- vs.... (More)
A second generation of a substrate-selective dynamic supramolecular catalytic system consisting of a catalyst part and a receptor part, connected by a hydrogen-bonding motif, has been realized based on rational design. The results from analyses of the equilibrium mixture of the species generated by the components of the first generation system led us to selectively lock the cisoid conformation of the catalyst part to increase the amount of the substrate-selective catalytic cavity in the equilibrium mixture. This was realized by strapping the catalyst part by organic synthesis. This strapping led to an increase in substrate selectivity in the pair-wise competitive epoxidations of pyridyl- vs. phenyl-appended styrenes and pyridyl- vs. phenyl-appended stilbenes of both Z- and E- configuration compared to the first generation system, reaching 3.4 : 1 as the highest substrate selectivity for Z-mono-pyridyl-stilbene (27a) vs. the corresponding all-carbon analogue (28a) and for E-dipyridyl-stilbene (26b) vs. the corresponding all-carbon analogue (28b), respectively. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic and Biomolecular Chemistry
volume
10
issue
10
pages
2059 - 2067
publisher
Royal Society of Chemistry
external identifiers
  • wos:000300374800018
  • pmid:22301724
  • scopus:84857604464
ISSN
1477-0539
DOI
10.1039/c2ob06859a
language
English
LU publication?
yes
id
c3920157-20dc-478a-a955-00878830f140 (old id 2367390)
date added to LUP
2012-03-06 17:15:54
date last changed
2017-09-03 03:06:37
@article{c3920157-20dc-478a-a955-00878830f140,
  abstract     = {A second generation of a substrate-selective dynamic supramolecular catalytic system consisting of a catalyst part and a receptor part, connected by a hydrogen-bonding motif, has been realized based on rational design. The results from analyses of the equilibrium mixture of the species generated by the components of the first generation system led us to selectively lock the cisoid conformation of the catalyst part to increase the amount of the substrate-selective catalytic cavity in the equilibrium mixture. This was realized by strapping the catalyst part by organic synthesis. This strapping led to an increase in substrate selectivity in the pair-wise competitive epoxidations of pyridyl- vs. phenyl-appended styrenes and pyridyl- vs. phenyl-appended stilbenes of both Z- and E- configuration compared to the first generation system, reaching 3.4 : 1 as the highest substrate selectivity for Z-mono-pyridyl-stilbene (27a) vs. the corresponding all-carbon analogue (28a) and for E-dipyridyl-stilbene (26b) vs. the corresponding all-carbon analogue (28b), respectively.},
  author       = {Sheibani, Esmaeil and Wärnmark, Kenneth},
  issn         = {1477-0539},
  language     = {eng},
  number       = {10},
  pages        = {2059--2067},
  publisher    = {Royal Society of Chemistry},
  series       = {Organic and Biomolecular Chemistry},
  title        = {Conformationally restricted dynamic supramolecular catalysts for substrate-selective epoxidations.},
  url          = {http://dx.doi.org/10.1039/c2ob06859a},
  volume       = {10},
  year         = {2012},
}