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Publicly Available Published by De Gruyter January 1, 2009

Stereocontrolled asymmetric synthesis

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

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.


Conference

International Conference on Organic Synthesis (ICOS-13), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 13th, Warsaw, Poland, 2000-07-01–2000-07-05


Published Online: 2009-01-01
Published in Print: 2000-01-01

© 2013 Walter de Gruyter GmbH, Berlin/Boston

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