149065-76-9Relevant articles and documents
Synthesis of modular thiophene-oxazoline ligands and their application in the asymmetric phenyl transfer reaction to aldehydes
Chai, Zhuo,Liu, Xin-Yuan,Wu, Xiao-Yu,Zhao, Gang
, p. 2442 - 2447 (2006)
A series of thiophene mono (oxazoline) N,O-ligands with three sites of diversity were synthesized concisely in two steps from the corresponding thiophene carbonitriles. These ligands were applied to the enantioselective phenyl transfer reaction of aldehydes, resulting in the corresponding chiral diaryl methanol products with excellent yields and moderate to good enantioselectivities.
The application of Hetphox ligands to the asymmetric intermolecular heck reaction of 2,3-dihydrofuran and 2,2-disubstituted-2,3-dihydrofurans
Kilroy, Tim G.,Cozzi, Pier Giorgio,End, Nicole,Guiry, Patrick J.
, p. 1879 - 1888 (2007/10/03)
A series of thiophene- and benzothiophene-oxazoline containing ligands, were applied in the intermolecular asymmetric phenylation and cyclohexenylation of 2,3-dihydrofuran 1. Phenylation proceeded in moderate to high chemical yields, with good regioselectivities and in up to 95% ee. Cyclohexenylations gave similarly high chemical yields and regioselectivities with the optimal result being a 96% yield of the major product in 97% ee. 2,2-Dialkyl-2,3- dihydrofurans were also tested as substrates and the phenylation and cyclohexenylation of 2,2-dimethyl-2,3-dihydrofuran proceeded in high yields and ee's up to 91% and 89%, respectively. The phenylation and cyclohexenylation of the 2,2-diethyl analogue proceeded in excellent yields and ee's up to 99% and 87%, respectively. For each substrate, palladium complexes formed from the t-butyl-substituted ligand 10 gave the highest yields, regioselectivities, and enantioselectivities over the broad range of reaction conditions studied. 2,2-Diisopropyl-2,3-dihydrofuran was prepared but was found to be unreactive in the intermolecular Heck reaction thus providing insight into to the steric limits for 2,3-dihydrofuran substrates.
Preparation of Novel Sulfur and Phosphorus Containing Oxazolines as Ligands for Asymmetric Catalysis
Allen, Joanne V.,Dawson, Graham J.,Frost, Christopher G.,Williams, Jonathan M. J.,Coote, Steven J.
, p. 799 - 808 (2007/10/02)
The preparation of enantiomerically pure ligands which contain both an oxazoline group and an additional sulfur or phosphorus donor atom are described.Methylthiomethyl, o-thioanisyl and thienyl oxazolines have been prepared in one step, and o-diphenylphosphinophenyl oxazolines have been prepared in two steps in good yields from commercially available starting materials.
