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Asymmetric Syntheses of 2-(1-Aminoethyl)phenols

Published in Helvetica Chimica Acta. 2004, vol. 87, no. 3, p. 561-579
Abstract Three different routes were probed for the synthesis of enantiomerically enriched 2-(1-aminoethyl)phenols and their methyl ethers. The first route centers on diastereoselective nucleophile addition to chiral imines. The second route has as key steps the enantioselective reduction of a ketone followed by nucleophilic substitution, and the third route involves a diastereoselective imine reduction. The efficiency of the approach depends on the substrate substitution pattern. All three methods work well for the parent compound 2-(1-aminoethyl)phenol (1) but the third route is the most efficient, providing the compound with >96% enantiomer excess in three steps with an overall yield of 71%. Conversely, for the ortho-methyl analogue 2, the first method is best. For the t-Bu-substituted analogue 3, only moderate enantiomeric enrichment was achieved.
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KUNDIG, Ernst Peter et al. Asymmetric Syntheses of 2-(1-Aminoethyl)phenols. In: Helvetica Chimica Acta, 2004, vol. 87, n° 3, p. 561-579. doi: 10.1002/hlca.200490054 https://archive-ouverte.unige.ch/unige:7833

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Deposited on : 2010-06-21

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