Exploiting phosphonate chemistry in metal-mediated dearomatization: Stereoselective construction of functionalized spirolactams from arene ruthenium complexes

FC Pigge, JJ Coniglio, R Dalvi

Index: Pigge, F. Christopher; Coniglio, John J.; Dalvi, Rashmi Journal of the American Chemical Society, 2006 , vol. 128, # 11 p. 3498 - 3499

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Citation Number: 45

Abstract

Arene ruthenium complexes possessing β-amido phosphonate side chains participate in intramolecular spirocyclization reactions to deliver stable cyclohexadienyl ruthenium adducts. Spirocyclization is accomplished via a tandem two-step sequence that involves stereoselective nucleophilic aromatic addition to the ipso position of the coordinated arene, followed by intermolecular Horner-Wadsworth-Emmons olefination. The resulting η5- ...