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The first enantio- and diastereoselective approach to both 2-(2′-oxiranyl)piperidines and to 2-(2′-oxiranyl)pyrrolidines is reported. The method relies on the Sharpless asymmetric epoxidation of allyl alcohols as the sole source of chirality, and involves as the key step the base-mediated cyclization of (α-aminoalkyl)oxiranes functionalized at the ε{lunate} (or δ) position. The asymmetric synthesis of (+)-α-conhydrine illustrates the applicability of this strategy to the preparation of biologically active 2-(1-hydroxyalkyl)piperidine alkaloids. © 2008 Elsevier Ltd. All rights reserved.




Rodríguez, D., Picó, A., & Moyano, A. (2008). A highly stereocontrolled route to 2-(2′-oxiranyl)piperidines and pyrrolidines: enantioselective synthesis of (+)-α-conhydrine. Tetrahedron Letters, 49(48), 6866–6869. https://doi.org/10.1016/j.tetlet.2008.09.095

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