Stereoselective preparation of spirane bridged, sandwiched bisarenes |
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Authors: | Marit Rolandsgard |
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Institution: | Department of Chemistry, University of Oslo, N-0315 Oslo, Norway |
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Abstract: | Preparation of α-oxo derivatives of spiro4.4]nonane, spiro4.5]decane and spiro5.5]undecane derivatives is described. An efficient method for spiroannulation by Rh(I)-catalysed intramolecular hydroacylation provides α,α′-difunctionalised spiro4.5]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. |
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Keywords: | α α&prime -cis cis-Diarylspiranes Spirane bridges Stereoselective hydrogenation Rh(I)-catalysed hydroacylation |
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