Ma Shengming, Xie Hexin
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. 2002 Sep 6;67(18):6575-8. doi: 10.1021/jo025967v.
Under the catalysis of 1 mol % Pd(PPh3)4, the reaction of 4,4-disubstituted 2,3-allenamides and organic iodides in toluene afforded iminolactones stereospecifically in >90% yields using K2CO3 (2 equiv)-5 mol % TBAB as the base. A similar reaction with 4-monosubstituted 2,3-allenamides afforded gamma-hydroxy-gamma-lactams in relatively lower yields. The N/O-attack selectivity may be determined by the steric effect at the 4-position of 2,3-allenamides.
在1 mol% Pd(PPh₃)₄的催化下，4,4 - 二取代的2,3 - 联烯酰胺与有机碘化物在甲苯中反应，以碳酸钾（2当量）- 5 mol% 四丁基溴化铵作为碱，立体专一性地生成亚胺内酯，产率>90%。4 - 单取代的2,3 - 联烯酰胺的类似反应以相对较低的产率生成γ - 羟基 - γ - 内酰胺。N/O - 进攻选择性可能由2,3 - 联烯酰胺4 - 位的空间效应决定。
