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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

IMPACT FACTOR increased in 2015: 2.615
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Rank 60 out of 163 in category Chemistry, Multidisciplinary in the 2015 Thomson Reuters Journal Citation Report/Science Edition

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Asymmetric synthesis by stereocontrol

Yong Hae Kim1 / Sam Min Kim1 / So Won Youn1

1Center for Molecular Design and Synthesis, Department of Chemistry, Korea Advanced Institute of Science and Technology, Taejon, Korea


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

Citation Information: Pure and Applied Chemistry. Volume 73, Issue 2, Pages 283–286, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: 10.1351/pac200173020283, January 2009

Publication History

Published Online:

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.

Citing Articles

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