Asymmetric synthesis by stereocontrol*
Yong Hae Kim,** Sam Min Kim, and So Won Youn
Center for Molecular Design and Synthesis, Department
of Chemistry, Korea Advanced Institute of Science and Technology, Taejon,
Korea
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
a-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 a,b-unsaturated
amides coupled with SmI2 to dimerized products containing
two chiral carbons which were first obtained as the adjacent chiral
carbons.
* Lecture presented at the XIXth International Conference
on Organometallic Chemistry (XIX ICOMC) , Shanghai, China, 23-28 July
2000. Other presentations are published in this issue, pp. 205-376.
** Corresponding author
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