Pentaspiranes and hexaspiranes with 1,3-dioxane or 1,3-oxathiane rings: synthesis and stereochemistry

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 chi...

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Bibliographic Details
Published in:Tetrahedron 2004-03, Vol.60 (14), p.3173-3189
Main Authors: Terec, Anamaria, Grosu, Ion, Condamine, Eric, Breau, Livain, Plé, Gérard, Ramondenc, Yvan, Rochon, Fernande D, Peulon-Agasse, Valérie, Opris, Dorina
Format: Article
Language:English
Subjects:
Analytical chemistry
Chemical Sciences
Conformational analysis
Helical and axial chirality
Material chemistry
Organic chemistry
Polyspiranes
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.02.027