Ma Shengming, Yu Fei, Li Jing, Gao Wenzhong
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Chemistry. 2007;13(1):247-54. doi: 10.1002/chem.200600431.
The palladium-catalyzed coupling-cyclization of beta-amino allenes with organic halides ranging from aryl halide to 1-alkenyl halide was studied. 2,3-Dihydro-1H-pyrroles were obtained by reaction of 3-substituted-5-unsubstituted-3,4-allenyl amides under conditions A, while the reaction of 5-substituted-3,4-allenyl amides afforded 1,2,5,6-tetrahydropyridines and/or azetidines with high de under conditions B or C. The skeleton and relative configuration of the six-membered products were established by the X-ray diffraction studies of 10 ka. Allenyl amide 4 q reacted with 1,4-diiodobenzene 6 r to afford double cyclization product 15. The structure of its major stereoisomer was also determined by the X-ray diffraction study.
研究了钯催化的β-氨基丙二烯与从芳基卤化物到1-烯基卤化物的有机卤化物的偶联环化反应。在条件A下，3-取代-5-未取代-3,4-丙二烯基酰胺反应得到2,3-二氢-1H-吡咯，而在条件B或C下，5-取代-3,4-丙二烯基酰胺反应以高非对映体过量得到1,2,5,6-四氢吡啶和/或氮杂环丁烷。通过对10 ka的X射线衍射研究确定了六元产物的骨架和相对构型。丙二烯基酰胺4 q与1,4-二碘苯6 r反应得到双环化产物15。其主要立体异构体的结构也通过X射线衍射研究确定。
