Immobilization of chiral amide derived from (1R,2S)-(-)-norephedrine over 3D nanoporous silica for the enantioselective addition of diethylzinc to aldehydes

Balakrishnan, Umesh, Ananthi, Nallamuthu, Velmathi, Sivan, Benzigar, Mercy R., Talapaneni, Siddulu N., Aldeyab, Salem S., Ariga, Katsuhiko and Vinu, Ajayan (2012) Immobilization of chiral amide derived from (1R,2S)-(-)-norephedrine over 3D nanoporous silica for the enantioselective addition of diethylzinc to aldehydes. Microporous and Mesoporous Materials, 155 1: 40-46. doi:10.1016/j.micromeso.2012.01.005


Author Balakrishnan, Umesh
Ananthi, Nallamuthu
Velmathi, Sivan
Benzigar, Mercy R.
Talapaneni, Siddulu N.
Aldeyab, Salem S.
Ariga, Katsuhiko
Vinu, Ajayan
Title Immobilization of chiral amide derived from (1R,2S)-(-)-norephedrine over 3D nanoporous silica for the enantioselective addition of diethylzinc to aldehydes
Journal name Microporous and Mesoporous Materials   Check publisher's open access policy
ISSN 1387-1811
1873-3093
Publication date 2012-06
Sub-type Article (original research)
DOI 10.1016/j.micromeso.2012.01.005
Volume 155
Issue 1
Start page 40
End page 46
Total pages 7
Place of publication Amsterdam, Netherlands
Publisher Elsevier
Collection year 2013
Language eng
Abstract Chiral amide synthesized from (1R,2S)-(-)-norephedrine has been successfully immobilized onto three dimensional Ia3d cubic nanoporous material. The immobilization of the chiral amide has been confirmed by using various physiochemical techniques. The immobilized ligand has been screened for its catalytic activity in the enantioselective addition of diethylzinc to aromatic aldehydes. The immobilized catalyst was found to be highly active and selective, affording the final product chiral alcohols in 92% yield with a 95% ee at room temperature. The enantioselectivity of the immobilized catalyst is much higher than that of the homogenous catalyst (40% ee) at room temperature. In addition, the catalyst was stable and found to be purely heterogeneous and recyclable. The activity of the immobilized catalyst has been also investigated for the aromatic aldehydes with different electron donating and withdrawing groups. In addition, the electronic and steric effects of the substrates affecting the activity and the enantioselectivity of the catalysts were discussed in detail.
Keyword Heterogeneous catalysis
Nanoporous
Diethylzinc addition
Chiral synthesis
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
Australian Institute for Bioengineering and Nanotechnology Publications
 
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