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Pure Appl. Chem., 2012, Vol. 84, No. 7, pp. 1651-1657

http://dx.doi.org/10.1351/PAC-CON-11-10-16

Published online 2012-06-05

Chiral 2,6-bis(5',5'-diphenyloxazoline)pyridine as an efficient ligand for asymmetric catalysis

Pradeep K. Singh1 and Vinod K. Singh2,1*

1 Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India
2 Department of Chemistry, Indian Institute of Science Education and Research Bhopal, ITI Campus (Gas Rahat) Building, Govindpura, Bhopal 460 023, India

Abstract: A modified tridentate pyridine bisoxazoline (pybox) ligand, possessing gem-diphenyl substitution at C-5 of the oxazoline rings, has been proved to be a very efficient ligand for enantioselective allylic oxidation, one-pot three-component synthesis of propargy-amines, and Friedel–Crafts alkylation of various aromatic compounds. We have shown that a 5',5'-diphenyl grouping in the oxazoline rings of chiral ligands is crucial for higher reaction rates as well as enhanced enantioselectivity.

Keywords

2,6-bis(5',5'-diphenyloxazoline)pyridine; allylic oxidation; asymmetric catalysis; enantioselective reaction; Friedel–Crafts reaction; propargylamine; pyridine-bisoxazoline gem-diphenyl (pybox-diph).

Conference

23rd International Conference on Heterocyclic Chemistry (ICHC-23), Glasgow, UK, 31 July–4 August 2011
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References (29) Other PAC articles by these authors