Stereocontrolled asymmetric synthesis

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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 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 for the first time depending on the structure of α-ketoamides.

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Kim, Y. H., Kim, S. M., Park, D. H., & Youn, S. W. (2000). Stereocontrolled asymmetric synthesis. In Pure and Applied Chemistry (Vol. 72, pp. 1691–1697). Walter de Gruyter GmbH. https://doi.org/10.1351/pac200072091691

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