Palladium-mediated carbosubstitutions in spiranes

ML Falck-Pedersen, C Rømming, K Undheim

Index: Falck-Pedersen, Mette Lene; Romming, Christian; Undheim, Kjell Tetrahedron, 1999 , vol. 55, # 28 p. 8525 - 8538

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Citation Number: 16

Abstract

Carbosubstitutions in spirene triflates can be effected by Pd-catalyzed couplings with stannylated or zincated arenes. Differential carbosubstitution resulted from stepwise triflation and coupling in spiro [4, 4]-nonane-1, 6-dione. Catalytic hydrogenation of the 1, 6-diphenyl- 1, 6-diene gave the cis, cis-disubstituted spirane. Metal hydride reduction of intermediate monoketone gave mainly the cis-alcohol.