Merging allylic carbon-hydrogen and selective carbon-carbon bond activation.
Nature
; 505(7482): 199-203, 2014 Jan 09.
Article
en En
| MEDLINE
| ID: mdl-24317692
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.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Nature
Año:
2014
Tipo del documento:
Article
País de afiliación:
Israel