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Synthesis 2000; 2000(10): 1444-1448
DOI: 10.1055/s-2000-7101
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Synthesis of Optically Active 3-Amino-2,3-dihydrobenzopyran-4-ones by Ring Transformation of Aziridinecarboxamides

Karsten Woydowski* , Jürgen Liebscher
  • *Institut für Chemie, Humboldt-Universität Berlin, Hessische Straße 1-2, 10115 Berlin, Germany; Fax + 49(30)20 93 89 07; E-mail: liebscher@chemie.hu-berlin.de
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Publication Date:
31 December 2000 (online)

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Weinreb amides 1 of aziridinecarboxylic acids react with o-lithiated O-methoxymethylphenols 2 to 2-benzoylaziridines 3 which, after O-deprotection, undergo ring transformation by attack of the phenolic hydroxy group at 3-position of the aziridine ring affording optically active 3-aminodihydrobenzopyran-4-ones 5 under acidic conditions. Alternatively, 5-membered benzofuran-3-ones 6 and 7 can be obtained under basic conditions.

2,3-dihydrobenzopyran-3-one - aziridines - ring transformation - benzofuran-3-ones - asymmetric synthesis