期刊
HELVETICA CHIMICA ACTA
卷 87, 期 3, 页码 561-579出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.200490054
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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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