Journal of the American Chemical Society, Vol.130, No.45, 14960-14960, 2008
Asymmetric Synthesis of Bicyclo[4.3.1]decadienes and Bicyclo[3.3.2]decadienes via [6+3] Trimethylenemethane Cycloaddition with Tropones
The cyanosubstituted trimethylenemethane donor undergoes (palladium-catalyzed [6 + 3] cycloaddition with a variety of tropones to yield bicycle[4.3.1]decadienes in excellent regio-, diastereo-, and enantioselectivity. Products of the Pd-TMM [6 + 3] cycloaddition participate in a thermal [3,3] sigmatropic rearrangement to yield bicycle[3.3.2]decadienes in good yield.