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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

journal contribution
posted on 09.01.2014, 14:46 by Patricia E. Standen, Dharati Dodia, Mark Elsegood, Simon J. Teat, Marc Kimber
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.

History

School

  • Science

Department

  • Chemistry

Citation

STANDEN, P.E. ... et al, 2012. 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. Organic and Biomolecular Chemistry, 10 (43), pp. 8669 - 8676

Publisher

© The Royal Society of Chemistry

Version

VoR (Version of Record)

Publication date

2012

Notes

This article is closed access, it was published in the journal Organic and Biomolecular Chemistry [© The Royal Society of Chemistry]. The definitive version is available at: http://dx.doi.org/10.1039/c2ob26784e

ISSN

1477-0520

Language

en

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