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Journal article

A novel oxidative cyclisation onto vinyl silanes.

Abstract:
A novel osmium-catalysed oxidative cyclisation of 1,2-diols bearing a pendant vinyl silane affords THFs that contain silicon functionality at the ring junction. When the cyclisation occurs onto a vinyl benzyldimethylsilyl group, the resulting silyl group can act as a masked hydroxyl group and undergo a Fleming-Tamao type oxidation at a later stage to form the corresponding lactol. The scope of this reaction can also be extended beyond 1,2-diols and applied to the cyclisation of α-hydroxy-sulfonamides and α-hydroxy-amides.
Publication status:
Published

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Publisher copy:
10.1039/c0cc01342k

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Chemical communications (Cambridge, England)
Volume:
46
Issue:
39
Pages:
7310-7312
Publication date:
2010-10-05
DOI:
EISSN:
1364-548X
ISSN:
1359-7345
URN:
uuid:988712c6-d5f7-4304-8a78-18a3440cef9a
Source identifiers:
71177
Local pid:
pubs:71177
Language:
English
Keywords:

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