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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Bibliographic Details
Published in:Organic letters Vol. 12; no. 4; pp. 684 - 687
Main Authors: Zacuto, Michael J, Tomita, Daisuke, Pirzada, Zainab, Xu, Feng
Format: Journal Article
Language:English
Published: United States American Chemical Society 19-02-2010
Subjects:
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Hexosamines - chemical synthesis
Hexosamines - chemistry
Molecular Structure
Pyrans - chemical synthesis
Pyrans - chemistry
Ruthenium - chemistry
Stereoisomerism
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol9026667