345269-80-9Relevant academic research and scientific papers
Sequential stereoselective catalysis: Two single-flask reactions of a substrate in the presence of a bifunctional chiral ligand and different transition metals
Annunziata, Rita,Benaglia, Maurizio,Cinquini, Mauro,Cozzi, Franco,Puglisi, Alessandra
, p. 1428 - 1432 (2007/10/03)
A new bifunctional ligand capable of promoting different stereoselective catalytic transformations in combination with different transition metals has been prepared by connecting with a spacer a bis(oxazoline) to dihydroquinidine; this ligand was employed in a one-flask procedure in which methyl (E)-3-(4-vinylphenyl)propenoate underwent first cyclopropanation at the electron-rich double bond and then dihydroxylation at the electron-poor alkene to afford a product containing four stereocenters with complete regiocontrol and high stereoselectivity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Poly(ethylene glycol)-supported bisoxazolines as ligands for catalytic enantioselective synthesis
Annunziata,Benaglia,Cinquini,Cozzi,Pitillo
, p. 3160 - 3166 (2007/10/03)
Two chiral bisoxazolines (box) supported on a modified poly(ethylene glycol) (PEG) have been prepared by a reaction sequence that involved formation of the properly functionalized box and their attachment to the polymer matrix by means of a spacer and a linker. The solubility properties of PEG allowed use of the supported box as ligands in some catalytic asymmetric transformations carried out under homogeneous conditions and to recover the ligands as if bound to an insoluble support. When the supported box were employed in combination with Cu(II) salts in the Diels-Alder cycloaddition between cyclopentadiene and N-acryloyloxazolidinone, low levels of enantioselectivity were observed (up to 45% ee). Much better results were obtained in the cyclopropanation of styrenes carried out in the presence of CuOTf (up to 93% ee) and in the ene-reaction between α-methylstyrene or methylenecyclohexane and ethylglyoxalate (up to 95% ee). One of the ligands, readily recovered by precipitation and filtration, was recycled two times in the ene-reaction with marginal loss in the catalytic activity and very limited erosion of the enantioselectivity.
