Diastereoselective Synthesis of Hexahydro-3H-pyrrolyzin-3-ones through Pd-Catalyzed Carboamination
Diastereoselective Synthesis of Hexahydro-3H-pyrrolyzin-3-ones through Pd-Catalyzed Carboamination
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DOI：
10.1021/jo1002032
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发表时间：
2010-03-19
影响因子：
3.6
通讯作者：
Tiecco, Marcello
中科院分区：
文献类型：
--
作者：
Bagnoli, Luana;Cacchi, Sandro;Tiecco, Marcello
容易获得的（5 R）-5-丁-3-烯-1-基吡咯烷-2-酮与芳基溴化物、氯化物或三氟甲磺酸酯在Pd-2（dba）（3）、Xphos和Cs2 CO 3存在下在1，4-二氧六环中在120 ℃下反应，通过非对映选择性碳胺化反应以良好至高产率得到（5 R，7aR）-5-芳基六氢吡咯烷-3-酮。芳基碘是比溴化物和氯化物更不成功的底物。
The reaction of readily available (5R)-5-but-3-en-1-ylpyrrolidin-2-one with aryl bromides, chlorides, or triflates in the presence of Pd-2(dba)(3), Xphos, and Cs2CO3 in 1,4-dioxane at 120 degrees C affords (5R,7aR)-5-aryl hexahydropyrrolizidin-3-ones in good to high yields through a diastereoselective carboamination reaction. Aryl iodides are less successful substrates than bromides and chlorides.