Resolution of limonene 1,2-epoxide diastereomers by mercury(II) ions
article
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.
TNO Identifier
57162
ISSN
00404039
Source
Tetrahedron Letters, 42(12), pp. 5521-5524.
Pages
5521-5524
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