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A New Target for Highly Stereoselective Katsuki–Sharpless Epoxidation – One-Pot Synthesis ofC2-Symmetric 2,2′-Bioxiranes
- Source :
- European Journal of Organic Chemistry. 2007:758-767
- Publication Year :
- 2007
- Publisher :
- Wiley, 2007.
-
Abstract
- The double asymmetric Katsuki–Sharpless epoxidation of a conjugated diallyl alcohol affords excellent enantioselectivity (>97 % ee), the product being isolated as the stable p-nitrobenzoate 5a or tosylate 5b. The optical purities of the chiral epoxides were determined by HPLC on chiral columns, while the molecular structures of compounds 5a and 7 and the absolute configuration of mono-epoxide 12 were confirmed by X-ray crystallography. Possible π–π stacking interaction has been evaluated by ab initio calculation.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Details
- ISSN :
- 10990690 and 1434193X
- Volume :
- 2007
- Database :
- OpenAIRE
- Journal :
- European Journal of Organic Chemistry
- Accession number :
- edsair.doi...........f773c43b26c0a0fe8a70ef5d5ab63c95