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Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 2053-2059

http://dx.doi.org/10.1351/pac200577122053

Dual enantioselective control by heterocycles of (S)-indoline derivatives

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

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

Abstract: Diastereo-and enantioselective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure (S,S)- or (R,R)-2,3-dialkyltartaric acid and derivatives can be synthesized. Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene in the presence of Lewis acids proceed with high diastereofacial selectivity, giving either endo-R or endo-S products depending on Lewis acid and the structures of chiral dienophiles.