Merging allylic carbon-hydrogen and selective carbon-carbon bond activation

Ahmad Masarwa, Dorian Didier, Tamar Zabrodski, Marvin Schinkel, Lutz Ackermann, Ilan Marek

Research output: Contribution to journalArticlepeer-review

Abstract

Since the nineteenth century, many synthetic organic chemists have focused on developing new strategies to regio-, diastereo-and enantioselectively build carbon-carbon and carbon-heteroatom bonds in a predictable and efficient manner. Ideal syntheses should use the least number of synthetic steps, with few or no functional group transformations and by-products, and maximum atom efficiency. One potentially attractive method for the synthesis of molecular skeletons that are difficult to prepare would be through the selective activation of C-H and C-C bonds, instead of the conventional construction of new C-C bonds. Here we present an approach that exploits the multifold reactivity of easily accessible substrates with a single organometallic species to furnish complex molecular scaffolds through the merging of otherwise difficult transformations: allylic C-H and selective C-C bond activations. The resulting bifunctional nucleophilic species, all of which have an all-carbon quaternary stereogenic centre, can then be selectively derivatized by the addition of two different electrophiles to obtain more complex molecular architecture from these easily available starting materials.

Original languageAmerican English
Pages (from-to)199-203
Number of pages5
JournalNature
Volume505
Issue number7482
DOIs
StatePublished - 2014

All Science Journal Classification (ASJC) codes

  • General

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