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Pseudo-C2-Symmetric Bimetallic Bissalen Catalysts for Efficient and Enantioselective Ring-Opening of meso-Epoxides

Dayou, Ma LU ; Xiao, Zeyun LU ; Etxabe, Julen and Wärnmark, Kenneth LU (2012) In ChemCatChem 4(9). p.1321-1329
Abstract
Bimetallic catalysts have been synthesised based on Jacobsens C2-symmetric bissalen ligand. They constitute the first examples of compounds with pseuodo-C2 symmetry, owing to the presence of two different metal ions. They have been investigated in the ring-opening of meso-epoxides by trimethylsilyl azide (TMSN3). Pseudo-C2-symmetric [CrIII?Co]bissalen complexes were the best in inducing ee (9394?%) in the ring-opened product of cyclohexene oxide by TMSN3 under solvent-free conditions, whereas a pseudo-C2-symmetric [CrIII?MnIII]-bissalen complex displayed the highest turnover frequency (183 h-1) but induced a lower ee (66?%). A broad substrate scope was displayed by a pseudo-C2-symmetric [CrIII?Co]bissalen catalyst: at 0.1 mol?% catalytic... (More)
Bimetallic catalysts have been synthesised based on Jacobsens C2-symmetric bissalen ligand. They constitute the first examples of compounds with pseuodo-C2 symmetry, owing to the presence of two different metal ions. They have been investigated in the ring-opening of meso-epoxides by trimethylsilyl azide (TMSN3). Pseudo-C2-symmetric [CrIII?Co]bissalen complexes were the best in inducing ee (9394?%) in the ring-opened product of cyclohexene oxide by TMSN3 under solvent-free conditions, whereas a pseudo-C2-symmetric [CrIII?MnIII]-bissalen complex displayed the highest turnover frequency (183 h-1) but induced a lower ee (66?%). A broad substrate scope was displayed by a pseudo-C2-symmetric [CrIII?Co]bissalen catalyst: at 0.1 mol?% catalytic loading and under solvent-free conditions, it induced the highest ee to date in the ring-opened product of a range of different meso-epoxides by using TMSN3. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
asymmetric catalysis, enantioselectivity, heterometallic complexes, ring-opening, transition metals
in
ChemCatChem
volume
4
issue
9
pages
1321 - 1329
publisher
John Wiley & Sons
external identifiers
  • wos:000308037400015
  • scopus:84865579375
ISSN
1867-3880
DOI
10.1002/cctc.201200018
language
English
LU publication?
yes
id
11a44c94-2ca6-4ca8-8777-3bfd5ca6a2e0 (old id 3146820)
date added to LUP
2012-11-26 09:28:31
date last changed
2017-01-01 03:23:22
@article{11a44c94-2ca6-4ca8-8777-3bfd5ca6a2e0,
  abstract     = {Bimetallic catalysts have been synthesised based on Jacobsens C2-symmetric bissalen ligand. They constitute the first examples of compounds with pseuodo-C2 symmetry, owing to the presence of two different metal ions. They have been investigated in the ring-opening of meso-epoxides by trimethylsilyl azide (TMSN3). Pseudo-C2-symmetric [CrIII?Co]bissalen complexes were the best in inducing ee (9394?%) in the ring-opened product of cyclohexene oxide by TMSN3 under solvent-free conditions, whereas a pseudo-C2-symmetric [CrIII?MnIII]-bissalen complex displayed the highest turnover frequency (183 h-1) but induced a lower ee (66?%). A broad substrate scope was displayed by a pseudo-C2-symmetric [CrIII?Co]bissalen catalyst: at 0.1 mol?% catalytic loading and under solvent-free conditions, it induced the highest ee to date in the ring-opened product of a range of different meso-epoxides by using TMSN3.},
  author       = {Dayou, Ma and Xiao, Zeyun and Etxabe, Julen and Wärnmark, Kenneth},
  issn         = {1867-3880},
  keyword      = {asymmetric catalysis,enantioselectivity,heterometallic complexes,ring-opening,transition metals},
  language     = {eng},
  number       = {9},
  pages        = {1321--1329},
  publisher    = {John Wiley & Sons},
  series       = {ChemCatChem},
  title        = {Pseudo-C2-Symmetric Bimetallic Bissalen Catalysts for Efficient and Enantioselective Ring-Opening of meso-Epoxides},
  url          = {http://dx.doi.org/10.1002/cctc.201200018},
  volume       = {4},
  year         = {2012},
}