Stereocontrolled asymmetric synthesis*
Yong Hae Kim**, Sam Min Kim, Doo Han Park, and So Won Youn
Center for Molecular Design and Synthesis, Department
of Chemistry, Korea Advanced Institute of Science and Technology, 305-701,
Taejon, Korea
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 a-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 a-ketoamides.
*Lecture presented at the 13th International
Conference on Organic Synthesis (ICOS-13), Warsaw, Poland, 1-5 July
2000.
** Corresponding author
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