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Publicly Available Published by De Gruyter January 1, 2009

Asymmetric synthesis by stereocontrol

Yong Hae Kim , Sam Min Kim and So Won Youn

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.


Conference

International Conference on Organometallic Chemistry (XIX ICOMC), International Conference on Organometallic Chemistry, ICOMC, Organometallic Chemistry, XIXth, Shanghai, China, 2000-07-23–2000-07-28


Published Online: 2009-01-01
Published in Print: 2001-01-01

© 2013 Walter de Gruyter GmbH, Berlin/Boston

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