Issue 39, 2010

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.

Graphical abstract: A novel oxidative cyclisation onto vinyl silanes

Supplementary files

Article information

Article type
Communication
Submitted
11 May 2010
Accepted
17 Aug 2010
First published
06 Sep 2010

Chem. Commun., 2010,46, 7310-7312

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements