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Pure Appl. Chem., 2001, Vol. 73, No. 2, pp. 283-286

Asymmetric synthesis by stereocontrol

Yong Hae Kim*, Sam Min Kim and So Won Youn

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

Abstract: 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. 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. Furthermore, it was demonstrated that α,β-unsaturated amides coupled with SmI2 to dimerized products containing two chiral carbons which were first obtained as the adjacent chiral carbons.