Chemoselectivity of the Ru-Catalyzed Cycloisomerization Reaction for the Synthesis of Dihydropyrans; Application to the Synthesis of l-Forosamine

Chemoselectivity of the Ru-Catalyzed Cycloisomerization Reaction for the Synthesis of Dihydropyrans; Application to the Synthesis of l-Forosamine

The chemoselectivity of a Ru-catalyzed cycloisomerization reaction has been established. The preference for O- capture of the vinylidene intermediate allows for the synthesis of 4-aminodihydropyrans that are valuable synthetic intermediates. The synthetic utility of these structures has been demonst...

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Veröffentlicht in:Organic letters 2010-02, Vol.12 (4), p.684-687
Hauptverfasser: Zacuto, Michael J, Tomita, Daisuke, Pirzada, Zainab, Xu, Feng
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Hexosamines - chemical synthesis
Hexosamines - chemistry
Molecular Structure
Pyrans - chemical synthesis
Pyrans - chemistry
Ruthenium - chemistry
Stereoisomerism
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Zusammenfassung:The chemoselectivity of a Ru-catalyzed cycloisomerization reaction has been established. The preference for O- capture of the vinylidene intermediate allows for the synthesis of 4-aminodihydropyrans that are valuable synthetic intermediates. The synthetic utility of these structures has been demonstrated in the synthesis of l-forosamine.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9026667