The pincer complex (PNN)RuH(CO), with a de-aromatized pyridine in the ligand backbone, is shown to react with nitriles in a metal-ligand cooperative manner. This leads to the formation of a series of complexes with new Ru-N(nitrile) and C(ligand)-C(nitrile) bonds. The initial nitrile cycloaddition products, the ketimido complexes 3, have a Brønsted basic (nitrile-derived) Ru-N fragment. This is...

Camphor-derived oxazoline-N-oxides are versatile dipoles in a new kind of asymmetric [2+3] cycloadditions. Recent applications of this methodology allowed the stereoselective syntheses of several β-lactones natural products such as 1233A and tetrahydrolipstatine. Two formal syntheses of β-lactams antibiotics, β-methyl thienamycin and carpetimycin A, have also been achieved using this type of cy...

Benzonitrile oxide (la) reach with 1,1,2,2,3,3-hexamethyl-4,5-bis(methylene)cyclopen~e (5) to give a mixture of the 1,3-dipolar cycloaddition product 8 and the oxime 9. This reaction is 26 times slower than the corresponding reaction of la with 1,2-bis(methylene)cyclopentane (15), which exclusively yields the 2-isoxazoline 19. With the assumption that the oxime 9 is generated by a stepwise proc...

Abstract The hydration of nitriles is an important transformation because the resulting primary amides present a huge number applications in synthetic organic chemistry, as well industrial and pharmaceutical interest. Metallic compounds (complexes, oxides, nanoparticles) are known to catalyze by activating nitrile substrate, water molecule, or both partners, upon coordination. In this Minirevie...