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Pentaspiranes and hexaspiranes with 1,3-dioxane or 1,3-oxathiane rings: synthesis and stereochemistry |
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| Authors: | Anamaria Terec Eric Condamine Gérard Plé Fernande D Rochon Dorina Opris |
| Institution: | a Organic Chemistry Department and CSOFSTM, ”Babes-Bolyai” University, 11 Arany Janos str., RO-400028 Cluj-Napoca, Romania b Faculté des Sciences, Université de Rouen, IRCOF, UMR 6014, 76821 Mont Saint-Aignan, Cedex, France c Université du Québec à Montréal, CP 8888, Succ. Centre Ville, Montréal, Que., Canada H3C 3P8 |
| Abstract: | The synthesis and stereochemistry of the first reported pentaspiro- and hexaspiro-1,3-dioxane and polyspiro-1,3-oxathiane (from dispiro to hexaspiro) derivatives are described. The crystal structures of a dispiro- and tetraspiro-1,3-oxathiane were determined by X-ray diffraction methods. NMR and chiral column HPLC investigations in solution revealed flexible and semiflexible structures for which syn-anti, cis-trans and d,l isomers were observed. |
| Keywords: | Polyspiranes Conformational analysis Helical and axial chirality |
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