Studies on epoxidation of enantiomerically pure 2,3-dideoxy hex-2-enitols: a convenient access to highly functionalized enantiomerically pure tetrahydrofuran derivatives |
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| Affiliation: | 1. The Scientific Technological Center of Organic and Pharmaceutical Chemistry, Armenian Academy of Science, Institute of Fine Organic Chemistry of A.L. Mnjoyan, Ave. Azatutyan 26, Yerevan 0014, Armenia;2. Aristotle University of Thessaloniki, School of Pharmacy, Thessaloniki 54124, Greece;3. Dipartimento di Chimica G. Ciamician, Università degli Studi di Bologna, Bologna 40126, Italy;1. Department of Medicinal Plant Research and Traditional Medicine, National Institute for Pharmaceutical Research and Development, Idu Industrial Area, P.M.B. 21 Garki, Abuja, Nigeria;2. Department of Chemistry, Columbia University, USA;3. Department of Chemistry, Ahmadu Bello University, Zaria, Nigeria;4. Pax Herbal Clinic & Research Laboratories, Benedictine Monastery, PO Box 150, Ewu-Esan, Edo State, Nigeria;5. Department of Chemistry, University of Ibadan, Ibadan, Nigeria |
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| Abstract: | A detailed comparative study on the epoxidation of enantiomerically pure allylic alcohols 8–14 derived from their respective glycals with Sharpless, m-CPBA and Camp’s reagents was carried out in order to obtain 2,3-epoxy alcohols keeping in view the versatility of these synthons in synthetic chemistry for the preparation of various molecules of biological importance by suitable chemical transformations. During the course of this study, the Sharpless asymmetric epoxidation reaction was found to be an unprecedented alternative, due to its mild reaction conditions, for synthesizing highly functionalized enantiomerically pure tetrahydrofuran derivatives. A detailed mechanistic pathway of their formation has also been studied. |
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