Stereocontrolled asymmetric synthesis

Stereo differentiated asymmetric syntheses have been achieved by -indoline derivations. Diels-Alder cycloadditions of -indoline chiral acrylamides with cyclopentadiene proceed with high diastereofacial selectivity, giving either or products depending on Lewis acid and the structures of chiral dienophiles. Diastereo- and enantio-selective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure ( )- or ( )-2,3-dialkyltar-taric acid and derivatives can be synthesized for the first time depending on the structure of α-ketoamides.