| Autor: |
Kündig, E. Peter, Botuha, Candice, Lemercier, Gilles, Romanens, Patrick, Saudan, Lionel, Thibault, Sylvie |
| Zdroj: |
Helvetica Chimica Acta; March 2004, Vol. 87 Issue: 3 p561-579, 19p |
| Abstrakt: |
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. |
| Databáze: |
Supplemental Index |
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