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Scientific article
English

Asymmetric Syntheses of 2-(1-Aminoethyl)phenols

Contributors

Kundig, Ernst Peter; Botuha, Candice; Lemercier, Gilles; Romanens, Patrick; Saudan, Lionel; Thibault, Sylvie

Published in

Helvetica chimica acta, vol. 87, no. 3, p. 561-579

Publication date

2004

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.

UNIGE affiliation entities

Citation (ISO format)

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

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Article

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Journal ISSN

0018-019X
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Technical informations

Creation

21/06/2010 10:28:01

First validation

21/06/2010 10:28:01

Update

14/03/2023 15:46:53

Status update

14/03/2023 15:46:53

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