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
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.