Resolution of limonene 1,2-epoxide diastereomers by mercury(II) ions
| Autor: | Maurice C. R. Franssen, M.J. van der Werf, H. Jongejan |
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| Přispěvatelé: | Centraal Instituut voor Voedingsonderzoek TNO |
| Rok vydání: | 2001 |
| Předmět: |
Tris
Limonene epoxide Limonene Diastereomer resolution Organic Chemistry Inorganic chemistry Diastereomer Epoxide chemistry.chemical_element Mercury Organische Chemie Biochemistry Medicinal chemistry Mercury (element) Ion Reaction rate chemistry.chemical_compound chemistry Drug Discovery Acetone Complexation VLAG Nutrition |
| Zdroj: | Tetrahedron Letters, 12, 42, 5521-5524 Tetrahedron Letters, 42, 5521-5524 Tetrahedron Letters 42 (2001) |
| ISSN: | 0040-4039 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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