N-<i>p</i>-Toluenesulfonylpyrroles from 1,3-Dienes
作者:Peter J. Harrington、Ignacio H. Sanchez
DOI:10.1080/00397919408013816
日期:1994.1
Abstract 1,3-Dienes can be converted to N-p-toluenesulfonylpyrroles in two steps: 1) [4+2]-cycloaddition with N-sulfinyl-p-toluenesulfonamide and 2) conversion of the 3,6-dihydro-1,2-thiazine oxide adduct to a pyrrole using triethylamine-trimethylphosphite.
Suppressed β-Hydride Elimination in Palladium-Catalyzed Cascade Cyclization−Coupling Reactions: An Efficient Synthesis of 3-Arylmethylpyrrolidines
作者:Chi-Wan Lee、Kyung Seok Oh、Kwang S. Kim、Kyo Han Ahn
DOI:10.1021/ol0056426
日期:2000.5.1
A novel type of palladium-catalyzed cascade cyclization-coupling reaction that proceeds with suppressed beta-hydride elimination has been found. One of the N-sulfonyl oxygens is suggested to coordinatively stabilize an alkylpalladium intermediate, thus preventing the intermediate from the usual beta-elimination, This is the first sequential palladium-catalyzed coupling reaction where the Suzuki and Heck reactions can compete. The reaction provides an efficient synthetic route to 4-methylene-3-arylmethylpyrrolidines, which are not readily available by other routes.
GAONI, Y., TETRAHEDRON LETT., 1982, 23, N 19, 2051-2052