Heterocyclic Spiranes and Dispiranes via Enantioselective Phosphine-Catalyzed [3+2] Annulations

The synthesis of highly functionalized heterocyclic spiranes has been carried out by [3+2] cyclizations between allenoates and enones, under phosphine catalysis. Excellent enantioselectivity levels (ees up to 99%) have been attained in FerroPHANE‐promoted cyclizations of this class, leading to chira...

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Veröffentlicht in:	Advanced synthesis & catalysis 2012-02, Vol.354 (2-3), p.408-414
Hauptverfasser:	Duvvuru, Deepti, Pinto, Nathalie, Gomez, Catherine, Betzer, Jean-François, Retailleau, Pascal, Voituriez, Arnaud, Marinetti, Angela
Format:	Artikel
Sprache:	eng
Schlagworte:	[3+2] cyclization Catalysis Catalysts: preparations and properties Chemical Sciences Chemistry enantioselective organocatalysis Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry phosphines Preparations and properties spiro compounds sulfoxides Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Zusammenfassung:	The synthesis of highly functionalized heterocyclic spiranes has been carried out by [3+2] cyclizations between allenoates and enones, under phosphine catalysis. Excellent enantioselectivity levels (ees up to 99%) have been attained in FerroPHANE‐promoted cyclizations of this class, leading to chiral sulfides with unprecedented spiranic structures. The corresponding sulfoxides have been obtained then via a subsequent, highly diastereoselective oxidation of the prostereogenic sulfur centre.
ISSN:	1615-4150 1615-4169
DOI:	10.1002/adsc.201100748