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Synthesis 1986; 1986(4): 315-317
DOI: 10.1055/s-1986-31596
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Facile Conversion of Epoxides to Chlorohydrins with Titanium(IV) Chloride/ 1,8-Diazabicyclo[5.4.0]undec-7-ene

Carol-Lynn Spawn* , Gary J. Drtina, David F. Wiemer
  • *Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, U. S. A.
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Publication Date:
27 September 2002 (online)

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A series of epoxides has been converted to the analogous chlorohydrins by treatment with titanium(IV) chloride and 1,8-diazabicyclo[5.4.0-undec-7-ene. This procedure tolerates acetal protecting groups normally labile to aqueous acids, and, when used in conjunction with the Sharpless epoxidation protocols, it allows the preparation of chiral chlorodiols selectively protected at one hydroxy group.

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