Asymmetric Syntheses of 2-(1-Aminoethyl)phenols

Article Article scientifique Article Asymmetric Syntheses of 2-(1-Aminoethyl)phenols eng 2004 author Kundig Ernst Peter 26401 author Botuha Candice 506576 author Lemercier Gilles 116181 author Romanens Patrick 22629 author Saudan Lionel 29949 author Thibault Sylvie 126550 561-579 10.1002/hlca.200490054 0018-019X 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. Dewey 540 36 Département de chimie organique 141 false Helvetica chimica acta 87 3 af48b393-e826-49a0-8806-2bded04b22f9 Article Restricted file1.pdf 284871 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Asymmetric Syntheses of 2-(1-Aminoethyl)phenols	Helvetica chimica acta			2004	692	0

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Thibault, Sylvie