113261-21-5Relevant academic research and scientific papers
Stereoselective synthesis of N-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides
Bertrand, Myra Beaudoin,Wolfe, John P.
, p. 6447 - 6459 (2007/10/03)
The stereoselective synthesis of N-acyl- and N-Boc-protected pyrrolidines via Pd-catalyzed reactions of γ-(N-acylamino) alkenes and γ-(N-Boc-amino) alkenes with aryl bromides is described. These reactions effect formation of two bonds in a single operation and proceed with generally high levels of diastereoselectivity. In contrast to previously described reactions of γ-(N-arylamino) alkenes, these transformations proceed in high yield and high regioselectivity with both electron-rich and electron-deficient aryl bromides as well as vinyl bromide substrates.
New Routes to Heterocycles via Sulphenylation of Unsaturated Amides
Samii, Zakaria K. M. Abd El,Ashmawy, Mohamed I. Al,Mellor, John M.
, p. 2517 - 2522 (2007/10/02)
The reaction of manganese(III) acetate with diphenyl disulphide in dichloromethane-trifluoroacetic acid in the presence of N-allylacetamide, followed by hydrolysis, affords a vicinal hydroxy sulphide.Similarly, addition to N-allyltrifluoroacetamide affords hydroxy sulphide adducts, but with different regioselectivity.N-Allylbenzamide and other unsaturated benzamides under similar conditions give cyclic products, 4,5-dihydro-1,3-oxazoles.Homoallylic amides give 5,6-dihydro-4H-1,3-oxazines.Amides derived from pent-4-enylamine give substituted pyrrolidines by cyclisation through nitrogen, but N-hex-5-enylbenzamide gives only an acyclic adduct.Unsaturated carboxylic acids and unsaturated carboxamides are transformed in good yield into lactones under similar conditions.
