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Ru-catalyzed C-H activation of aminoacid derivatives: an effective strategy for the synthesis of N-hetero-bicyclic compounds

AutorRuiz Morte, Sara ; Urriolabeitia, Esteban P.
Fecha de publicación2015
CitaciónOMCOS18 (2015)
ResumenC-H bond activation catalyzed by transition metals is a very useful tool for the synthesis of high added value molecules. It allows the introduction of countless fragments in otherwise inactive C-H bonds. Furthermore, the presence of a directing group allows the reaction to occur regioselectively. We have reported the use of primary amines as efficient directing groups, enabling the regioselective synthesis of N-heterocycles such as (benzo)isoquinolines and fused pyridines. This process is catalyzed using nonexpensive Ru complexes, which have shown an increasing number of applications in catalytic C-H functionalizations along last years. Aminoacids are biologically important molecules and, due to the presence of the amino moiety, they are adequate candidates for directed metal-catalyzed C-H functionalization. Up to now, however, the N atom must be protected before the functionalization takes place in order to achieve efficient transformations, and this complicates the synthetic sequence. Therefore, the functionalization of N-unprotected aminoacid derivatives is still challenging. Herein we report the oxidative coupling of unprotected N-free phenylglycinates with unsaturated hydrocarbons (alkynes and alkenes), catalyzed by a Ru (II) complex. The reaction between methylphenylglycinate derivatives and a range of alkynes affords 3,4-substituted methylisoquinoline-1-carboxylates, while the coupling between N-free or N-substituted methylphenylglycinate derivatives and widely available alkenes gives substituted methylisoindoline-1-carboxylates. The interest of isoquinoline- and isoindoline-1-carboxylate skeletons resides in the fact that they are often found in compounds with pharmacological and biological activity, and they are also key synthetic intermediates.
DescripciónResumen del póster presentado al Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS) IUPAC International Symposium, celebrado en Sitges-Barcelona (España) del 28 de junio al 2 de julio de 2015.
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