The regioselective outcome of ring rearrangement metathesis transformations performed on bicyclo[2.2.2]oct-2-ene derivatives

Standen, Patricia E.; Kimber, Marc

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The regioselective outcome of ring rearrangement metathesis transformations performed on bicyclo[2.2.2]oct-2-ene derivatives

journal contribution

posted on 2014-01-09, 13:38 authored by Patricia E. Standen, Marc KimberMarc Kimber

Treatment of bicyclo[2.2.2]oct-2-en-7-one with organometallic reagents gives the addition products in good yield and moderate diastereoselectivities in favour of the syn-products. Subsequent exposure of these addition products to ruthenium catalysed ring rearrangement metathesis (RRM) conditions reveals significant product divergence as a consequence of the newly acquired stereocentre.

History

School

Science

Department

Chemistry

Citation

STANDEN, P.E. and KIMBER, M.C., 2013. The regioselective outcome of ring rearrangement metathesis transformations performed on bicyclo[2.2.2]oct-2-ene derivatives. Tetrahedron Letters, 54 (31), pp. 4098 - 4101

Publisher

Version

AM (Accepted Manuscript)

Publication date

2013

Notes

This article was published in the journal, Tetrahedron Letters [© Elsevier Ltd]. The definitive version is available at: http://dx.doi.org/10.1016/j.tetlet.2013.05.112