Issue 56, 2014
From the journal:

Chemical Communications

Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition†

Zachary A. Kasun,a   Laina M. Gearya  and  Michael J. Krische*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA
E-mail: mkrische@mail.utexas.edu
Fax: +1 613 9418447
Tel: +1 512 2325892

Abstract

A new method for the ring expansion of cyclic diols is described. Using improved conditions for the ruthenium(0) catalyzed cycloaddition of cyclic 1,2-diols with 1,3-dienes, fused [n.4.0] bicycles 3a–3r (n = 3–6) are formed, which upon exposure to iodosobenzene diacetate engage in oxidative cleavage to form the 9–12 membered rings 4a–4r.

Graphical abstract: Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition

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Article information

DOI
https://doi.org/10.1039/C4CC03983A
Article type
Communication
Submitted
21 Apr 2014
Accepted
28 May 2014
First published
03 Jun 2014

Chem. Commun., 2014,50, 7545-7547

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Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition

Z. A. Kasun, L. M. Geary and M. J. Krische, Chem. Commun., 2014, 50, 7545 DOI: 10.1039/C4CC03983A

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