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Pure Appl. Chem., 2000, Vol. 72, No. 9, pp. 1691-1697

Stereocontrolled asymmetric synthesis

Yong Hae Kim, Sam Min Kim, Doo Han Park and So Won Youn

Center for Molecular Design and Synthesis, Department of Chemistry, Korea Advanced Institute of Science and Technology, 305-701, Taejon, Korea

Abstract: Stereo differentiated asymmetric syntheses have been achieved by S-indoline derivations. Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene proceed with high diastereofacial selectivity, giving either endo-R or endo-S 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 (S,S)- or (R,R)-2,3-dialkyltar-taric acid and derivatives can be synthesized for the first time depending on the structure of α-ketoamides.