Ma Shengming, Yu Fei, Gao Wenzhong
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China.
J Org Chem. 2003 Jul 25;68(15):5943-9. doi: 10.1021/jo0342469.
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.
研究了钯催化的α-或β-氨基丙二烯与烯丙基卤化物的偶联环化反应，分别生成3-烯丙基-2,5-二氢吡咯和1,2,3,6-四氢吡啶。起始原料易于获得。通过对7i和9b的X射线衍射研究确定了两类产物的骨架。通过研究2b与3-氯-1-丁烯、1-氯-2-丁烯和π-烯丙基钯物种的反应以及(S)-2m和(R)-2n偶联环化的立体化学结果，认为目前的转化最有可能通过Pd(II)催化的途径进行，尽管不能完全排除Pd(0)途径。
