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Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation
Institute for Research in Biomedicine (IRB) and Department of Organic Chemistry, University of Barcelona, Baldiri Reixac, 10. 08028 Barcelona, Spain
* Author to whom correspondence should be addressed.
Received: 8 January 2010; in revised form: 9 February 2010 / Accepted: 20 February 2010 / Published: 23 February 2010
Abstract: An overview of the synthesis and applications of chiral 2,3-epoxy alcohols containing unsaturated chains is presented. One of the fundamental synthetic routes to these compounds is Sharpless asymmetric epoxidation, which is reliable, highly chemoselective and enables easy prediction of the product enantioselectivity. Thus, unsaturated epoxy alcohols are readily obtained by selective oxidation of the allylic double bond in the presence of other carbon-carbon double or triple bonds. The wide availability of epoxy alcohols with unsaturated chains, the versatility of the epoxy alcohol functionality (e.g. regio- and stereo-selective ring opening; oxidation; and reduction), and the arsenal of established alkene chemistries, make unsaturated epoxy alcohols powerful starting materials for the synthesis of complex targets such as biologically active molecules. The popularization of ring-closing metathesis has further increased their value, making them excellent precursors to cyclic compounds.
Keywords: asymmetric synthesis; sharpless asymmetric epoxidation; epoxide ring-opening; olefin metathesis; ring-closing metathesis
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Riera, A.; Moreno, M. Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation. Molecules 2010, 15, 1041-1073.
Riera A, Moreno M. Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation. Molecules. 2010; 15(2):1041-1073.
Riera, Antoni; Moreno, María. 2010. "Synthetic Applications of Chiral Unsaturated Epoxy Alcohols Prepared by Sharpless Asymmetric Epoxidation." Molecules 15, no. 2: 1041-1073.