1423218-79-4Relevant academic research and scientific papers
Access to Benzazepinones by Pd-Catalyzed Remote C-H Carbonylation of γ-Arylpropylamine Derivatives
Martínez-Mingo, Mario,Rodríguez, Nuria,Gómez Arrayás, Ramón,Carretero, Juan C.
supporting information, p. 4345 - 4349 (2019/06/14)
A general method for the construction of seven-membered rings through Pd-catalyzed C(sp2)-H carbonylation at the remote ?-position of γ-arylpropylamine derivatives, including chiral α-amino acids, has been developed using Mo(CO)6 as the CO source, furnishing richly functionalized benzo[c]azepin-1-one derivatives. The readily removable N-SO2Py protecting/directing group provides high levels of chemo-, regio- and diastereoselectivity. Furthermore, this method is amenable to the postsynthetic modification of complex molecules such as small peptides.
Palladium-catalyzed N-(2-pyridyl)sulfonyl-directed C(sp3)-H γ-arylation of amino acid derivatives
Rodriguez, Nuria,Romero-Revilla, Jose A.,Fernandez-Ibanez, M. Angeles,Carretero, Juan C.
, p. 175 - 179 (2013/04/24)
The direct Pd-catalyzed γ-arylation of amino acid esters bearing a removable N-(2-pyridyl)sulfonyl directing group is described. A variety of N-(2-pyridyl)sulfonamide amino acid derivatives, including α-quaternary amino acid and β-amino acid substrates, react with iodoarenes in the presence of Pd(OAc)2 to provide γ-arylated products in synthetically useful yields. An unprecedented remote C(sp3)-H arylation of dipeptides is presented, illustrating the compatibility of the method with the presence of the peptidic bond. The process occurs without racemization at the Cα center and the auxiliary controlling group can be easily installed and removed in the amino acid backbone. A bimetallic Pd II γ-metalated complex has been isolated and characterized showing the key role exerted by the (2-pyridyl)sulfonyl unit.
