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Resolution of limonene 1,2-epoxide diastereomers by mercury(II) ions

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Author: Werf, M. van der · Jongejan, H. · Franssen, M.C.R.
Type:article
Date:2001
Institution: Centraal Instituut voor Voedingsonderzoek TNO
Source:Tetrahedron Letters, 12, 42, 5521-5524
Identifier: 57162
doi: doi:10.1016/S0040-4039(01)01037-1
Keywords: Nutrition · Complexation · Diastereomer resolution · Limonene epoxide · Mercury

Abstract

When HgCl2 was added to a diastereomeric mixture of cis- and trans-(4S)-limonene 1,2-epoxide, the Hg(II) ions stereoselectively complexed to the cis epoxide, enabling ring opening by water. The resulting mercuric salt could be demetalated by treatment with NaBH4, giving a mixture of diastereomeric (1S,2S,4S)- and (1R,2R,4S)-diols. The remaining trans-(4S)-epoxide was obtained in >98% d.e. and 40% yield. For reactions on a larger scale, the most convenient reaction system was Hg(OAc)2 in 50% acetone/tris-HCl buffer pH 7.0. The reaction rate was affected by the pH, with pH 6-8 as optimum. © 2001 Elsevier Science Ltd. All rights reserved.