Issue 2, 2006
From the journal:

Organic & Biomolecular Chemistry

Synthesis of [6,n] cis-fused ring compounds via Cr-mediated dearomatisation–ring-closing metathesis

E. Peter Kündig,*a   Alejandro Bellido,a   Krishna P. Kaliappan,a   Andrew R. Papea  and  Sylvie Radixa  

* Corresponding authors

a Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, Geneva 4, Switzerland
E-mail: peter.kundig@chiorg.unige.ch
Fax: +41 22 379 3215
Tel: +41 22 379 6093

Abstract

cis-Fused [6,8], [6,7], [6,6] and [6,5] ring systems containing a cyclohexadiene ring unit, a cycloenone ring and a quaternary carbon at the ring junction were obtained in only two steps from [Cr(CO)3(η6-p-methoxyphenyl oxazoline)]. The sequence proceeds via diastereoselective addition of three C-substituents across an arene double bond, followed by allylation and ring closing metathesis (RCM). RAMP-hydrazone and (R)-isopropyloxazoline were used as chiral auxiliaries to provide, after removal of the auxiliaries, the enantiomerically highly enriched [6,7] cis-fused system.

Graphical abstract: Synthesis of [6,n] cis-fused ring compounds via Cr-mediated dearomatisation–ring-closing metathesis

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Article information

DOI
https://doi.org/10.1039/B513261D
Article type
Paper
Submitted
19 Sep 2005
Accepted
16 Nov 2005
First published
14 Dec 2005

Org. Biomol. Chem., 2006,4, 342-351

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Synthesis of [6,n] cis-fused ring compounds via Cr-mediated dearomatisation–ring-closing metathesis

E. P. Kündig, A. Bellido, K. P. Kaliappan, A. R. Pape and S. Radix, Org. Biomol. Chem., 2006, 4, 342 DOI: 10.1039/B513261D

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