The influence of ligand side chain on the enantioselectivity of Lewis acid catalyzed Diels-Alder reactions.
The enantioselective Lewis acid-catalyzed Diels-Alder reaction of 3-(2-propenoyl)-1,3-oxazolidin-2-one 8 with cyclopentadiene was examined using a series of chiral mox ligands 2-6, deferring in the side chain at 2-position of the chiral oxazoline and in the nature of the substituent at the chiral center (4-position) of the oxazoline ring, and a combination of N-[(1R)-2-chloro-1-phenylethyl]-2-[(4R)-4-phenyl-4,5-dihydrooxazol-2-yl]butyramide 2-MgI(2)-I(2) was the most efficient catalyst.
Yamauchi
Masashige
M
Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Japan. yamauchi@josai.ac.jp
Itai
Kazuhiro
K
Honda
Yuko
Y
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D008024:Ligands; D017616:Magnesium Compounds / Q000138:chemical synthesis*; D008958:Models, Molecular; D023303:Oxazolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D008024:Ligands; D017616:Magnesium Compounds; D023303:Oxazolidinones