Synthesis 2003(8): 1209-1214
DOI: 10.1055/s-2003-39403
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Hydroxyalkyl Heterocycles by Ring Transformation of Spiroepoxy Lactones with Binucleophiles

Andreas Otto, Jürgen Liebscher*
Institut für Chemie, Humboldt-Universität Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany
Fax: +49(30)20937552; e-Mail: liebscher@chemie.hu-berlin.de;
Further Information

Publication History

Received 26 January 2003
Publication Date:
26 May 2003 (online)

Abstract

Spiroepoxy lactones 2 and 3 were obtained by epoxidation of α-alkylidenelactones 1 with dimethyldioxirane. Reaction of spiroepoxy lactones 2 with binucleophiles gave access to a number of hydroxyalkyl heterocycles with interesting substituent patterns. Depending on both the kind of substituent at the oxirane ring as well as the type of the binucleophile, the spiroepoxy lactones react either as C3 or as C2 bielectrophilic building blocks giving 4-, 6- and 7-membered partially saturated N-and S-heterocycles 5, 6, 8, 9, 11 and 13.

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Full details have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-205880. Copies of the data can be obtained free of charge on apllication to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.