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Issue 39, 2010
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A novel oxidative cyclisation onto vinyl silanes

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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.

Graphical abstract: A novel oxidative cyclisation onto vinyl silanes

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Article information


Submitted
11 May 2010
Accepted
17 Aug 2010
First published
06 Sep 2010

Chem. Commun., 2010,46, 7310-7312
Article type
Communication

A novel oxidative cyclisation onto vinyl silanes

T. J. Donohoe, P. C. M. Winship, B. S. Pilgrim, D. S. Walter and C. K. A. Callens, Chem. Commun., 2010, 46, 7310
DOI: 10.1039/C0CC01342K

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