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Título: | Synthesis of Enantiopure 3-Hydroxypiperidines from Sulfinyl Dienyl Amines by Diastereoselective Intramolecular Cyclization and [2,3]-Sigmatropic Rearrangement |
Autor: | Simal, Carmen CSIC; Bates, Robert H. CSIC; Ureña, Mercedes CSIC; Giménez, Irene; Koutsou, Christina; Infantes, L. CSIC ORCID; Fernández de la Pradilla, Roberto CSIC ORCID; Viso, Alma CSIC ORCID | Fecha de publicación: | 2015 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 80: 7674-7692 (2015) | Resumen: | The highly diastereoselective base-promoted intramolecular cyclization of a variety of enantiopure sulfinyl dienyl amines provides novel sulfinyl tetrahydropyridines that are readily converted to 3-hydroxy tetrahydropyridines via sigmatropic rearrangement. The influence of N- and C- substituents on the process has been studied. Procedures to shorten the sequence such as the tandem cyclization followed by [2,3]-sigmatropic rearrangement, as well as cyclization of the free amine, under Boc- or ArSO- deprotection conditions have been examined. Good to excellent levels of selectivity are generally observed for the reported transformations (dr: 75/25 to >98/2). A novel protocol to access substituted amino dienyl sulfoxides is also reported. | URI: | http://hdl.handle.net/10261/128539 | DOI: | 10.1021/acs.joc.5b01307 | Identificadores: | doi: 10.1021/acs.joc.5b01307 issn: 0022-3263 e-issn: 1520-6904 |
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