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Publicly Available Published by De Gruyter January 1, 2009

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

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.


Conference

IUPAC International Conference on Heteroatom Chemistry (ICHAC-7), International Conference on Heteroatom Chemistry, ICHAC, Heteroatom Chemistry, 7th, Shanghai, China, 2004-08-21–2004-08-25


Published Online: 2009-01-01
Published in Print: 2005-01-01

© 2013 Walter de Gruyter GmbH, Berlin/Boston

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