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Race, Nicholas J; Faulkner, Adele; Fumagalli, Gabriele; Yamauchi, Takayuki; Scott, James S; Rydén-Landergren, Marie; Sparkes, Hazel A; Bower, John F
Chemical science (Cambridge), 03/2017, Letnik: 8, Številka: 3Journal Article
The first examples of highly enantioselective Narasaka-Heck cyclizations are described. A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5- cyclization of a range of oxime esters with sterically diverse trisubstituted alkenes to generate dihydropyrroles containing tetrasubstituted nitrogen-bearing stereocenters in 56 to 86% yield and 90 : 10 to 95 : 5 e.r. These processes are rare examples of reactions that proceed enantioselective migratory insertion of alkenes into Pd-N bonds, and the first where trisubstituted alkenes are used to generate tetrasubstituted stereocenters with high enantioselectivity.
