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Synlett 1992; 1992(3): 204-206
DOI: 10.1055/s-1992-21314
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Regioselective Conversion of Epoxides to Halohydrins by Titanium(IV) Halide-Lithium Halide Complex

Makoto Shimizu* , Akifumi Yoshida, Tamotsu Fujisawa
  • *Department of Chemistry for Materials, Mie University, Tsu, Mie 514, Japan
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Publikationsdatum:
08. März 2002 (online)

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On treatment with titanium(IV) halide-lithium halide complex at low temperature, a series of epoxides [e.g., 1,2-epoxy-4-phenylbutane (1)] are regioselectively converted into the corresponding halohydrins resulting from an attack of halogen atom at the less substituted carbon atom. This procedure tolerates various alcohol protecting groups normally labile to aqueous acids, thus 2,3-epoxy alcohols allow the preparation of 3-halo-1,2-diols 6 which are selectively protected on only one hydroxy group.