Issue 43, 2012
From the journal:

Organic & Biomolecular Chemistry

The stereochemical outcome of allyl magnesium and indium additions to 5-substituted norbornen-7-ones and its application to cis fused carbocycle formation viaring rearrangement metathesis†

Patricia E. Standen,a   Dharati Dodia,a   Mark R. J. Elsegood,a   Simon J. Teatb  and  Marc C. Kimber*a  

* Corresponding authors

a Department of Chemistry, Loughborough University, Leicestershire, UK
E-mail: M.C.Kimber@lboro.ac.uk
Tel: +44 (0)01509 22 2570

b ALS, Berkeley Laboratory, 1 Cyclotron Road, CA 94720, USA

Abstract

The addition of allyl magnesium and allyl indium reagents to a key TBS protected norbornenyl building block, synthesised in 6-steps from commercially available 1,1-dimethoxy-2,3,4,5-tetrachlorocyclopentadiene, has been achieved providing the syn addition products with high diastereoselectivity. The subsequent exposure of the addition products to metathesis conditions, in the presence of ethene, then provided cis fused[3.0.3]-carbocycles with very high regioselectivity, via a Ring Rearrangement Metathesis (RRM) transformation.

Graphical abstract: The stereochemical outcome of allyl magnesium and indium additions to 5-substituted norbornen-7-ones and its application to cis fused carbocycle formation via ring rearrangement metathesis

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Article information

DOI
https://doi.org/10.1039/C2OB26784E
Article type
Paper
Submitted
11 Sep 2012
Accepted
21 Sep 2012
First published
24 Sep 2012

Org. Biomol. Chem., 2012,10, 8669-8676

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The stereochemical outcome of allyl magnesium and indium additions to 5-substituted norbornen-7-ones and its application to cis fused carbocycle formation via ring rearrangement metathesis

P. E. Standen, D. Dodia, M. R. J. Elsegood, S. J. Teat and M. C. Kimber, Org. Biomol. Chem., 2012, 10, 8669 DOI: 10.1039/C2OB26784E

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