Studies on Pd(II)-Catalyzed Coupling−Cyclization of α- or β-Amino Allenes with Allylic Halides
                                
                                    
                                        作者:Shengming Ma、Fei Yu、Wenzhong Gao                                    
                                    
                                        DOI:10.1021/jo0342469
                                    
                                    
                                        日期:2003.7.1
                                    
                                    The palladium-catalyzed coupling-cyclization of alpha- or beta-amino allenes with allylic halides leading to 3-allylic 2,5-dihydropyrroles and 1,2,3,6-tetrahydropyridines, respectively, was studied. The starting materials are easily available. The skeletons of both two classes of products were established by the X-ray diffraction studies of 7i and 9b. Through the study of the reaction of 2b with 3-chloro-1-butene, 1-chloro-2-butene, and pi-allyl palladium species and the stereochemical outcome of the coupling cyclization of (S)-2m and (R)-2n, it is believed that the current transformation most likely proceeded via a Pd(II)-catalyzed pathway, although a Pd(0) pathway cannot be completely excluded.