Asymmetric synthesis of bicyclo[4.3.1]decadienes and bicyclo[3.3.2]decadienes via [6 + 3] trimethylenemethane cycloaddition with tropones |
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| Authors: | Trost Barry M McDougall Patrick J Hartmann Olaf Wathen Peter T |
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| Institution: | Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu |
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| Abstract: | The cyanosubstituted trimethylenemethane donor undergoes palladium-catalyzed 6 + 3] cycloaddition with a variety of tropones to yield bicyclo4.3.1]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 bicyclo3.3.2]decadienes in good yield. |
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