Marit Rolandsgard, Saad Baldawi, D. Sirbu
Apr 18, 2005
Citations
0
Influential Citations
20
Citations
Journal
Tetrahedron
Abstract
Abstract Preparation of α-oxo derivatives of spiro[4.4]nonane, spiro[4.5]decane and spiro[5.5]undecane derivatives is described. An efficient method for spiroannulation by Rh(I)-catalysed intramolecular hydroacylation provides α,α′-difunctionalised spiro[4.5]decanes. The α,α′-dioxo groups have been converted into vinyl triflates for arylation by Pd-catalysed cross-coupling reactions under Stille, Negishi or Suzuki conditions depending on relative reactivities. Stereoselective saturation of the conjugated aryl olefinic bonds by catalytic hydrogenation over Pd–carbon provides methodology for stereoselective preparation of α-aryl- and α,α′-cis,cis-diaryl spiranes, the latter with a sandwich like structure. Single crystal X-ray analyses have been used in the structural assignments.