Stereoselective Conjugate Addition-Enamination of α-Linear N-tert-Butanesulfinyl Ketimines with Nitroolefins
Stereoselective Conjugate Addition-Enamination of α-Linear N-tert-Butanesulfinyl Ketimines with Nitroolefins
复制标题
α-线性 N-叔丁亚磺酰基酮亚胺与硝基烯烃的立体选择性共轭加成-烯化
DOI：
10.1055/s-0040-1719925
复制
发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Lu Chong-Dao
中科院分区：
文献类型：
--
作者：
Yisimayili Nuermaimaiti;Chu Li-Feng;Feng Jie;Lu Chong-Dao
由α-直链N-叔丁基亚磺酰基酮亚胺去质子化得到的N-亚磺酰基金属烯胺与硝基烯烃通过立体选择性共轭加成反应得到了与α-支链亚磺酰基酮亚胺相反的Michael加成物。在过量碱（2. 5equivt-BuOK）存在下，α-线性酮亚胺的加成物进一步立体选择性地去质子化，得到相应的动力学可拆分的N-亚磺酰基（Z）-烯胺衍生物，产率高，立体选择性好。提出了一个反应模型，以合理化所观察到的立体化学。
N-Sulfinyl metalloenamines, generated by deprotonating α-linearN-tert-butanesulfinyl ketimines, reacted with nitroalkenes via stereoselective conjugate addition to give Michael adducts with opposite stereochemistry to that obtained using α-branched sulfinylketimines. In the presence of excess base (2.5 equivt-BuOK), the adducts derived from α-linear ketimines were further stereoselectively deprotonated to afford the corresponding kinetically favorableN-sulfinyl (Z)-enamine derivatives in good yields with good stereoselectivities. A reaction model was proposed to rationalize the observed stereochemistry.