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Title: 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
Authors: Standen, Patricia E.
Dodia, Dharati
Elsegood, Mark R.J.
Teat, Simon J.
Kimber, Marc C.
Issue Date: 2012
Publisher: © The Royal Society of 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
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.
Description: 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
Version: Published
DOI: 10.1039/c2ob26784e
URI: https://dspace.lboro.ac.uk/2134/13936
Publisher Link: http://dx.doi.org/10.1039/c2ob26784e
ISSN: 1477-0520
Appears in Collections:Closed Access (Chemistry)

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