Since the nineteenth century, most of the efforts of organic chemists have been directed towards developing strategies to regio-, diastereo- and enantioselectively build carbon-carbon and carbon-heteroatom bonds in a predictable and efficient manner while controlling all of the needed stereochemical centers. Is the creation of new bond the only approach that organic chemists should follow? Could we design the synthesis of challenging molecular skeleton no more through the construction of carbon-carbon bonds but rather through selective activation of bonds? Herein, we present an alternative and unique approach that exploits multifold reactivity of easily accessible substrates with a single organometallic species so as to furnish advanced molecular scaffolds through a unique merging of otherwise challenging transformations: allylic C-H and selective C-C bond activations. The resulting bifunctional nucleophilic species, possessing an all-carbon quaternary stereogenic center, can further be selectively derivatized by the addition of two different electrophiles to give more complex molecular architecture from these easily available starting materials.

Merging allylic C-H and selective C-C bond activation en route to all-carbon quaternary stereogenic centers in acyclic systems

247th National Meeting (2014)

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