Cho Chang-Woo, Kong Jong-Rock, Krische Michael J
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA.
Org Lett. 2004 Apr 15;6(8):1337-9. doi: 10.1021/ol049600j.
Exposure of Morita-Baylis-Hillman (MBH) acetates to tertiary phosphine catalysts in the presence of 4,5-dichlorophthalimide enables regiospecific allylic substitution through a tandem S(N)2'-S(N)2' mechanism. Through the use of the chiral phosphine catalyst (R)-Cl-MeO-BIPHEP, chiral racemic MBH acetate 4 is converted to the corresponding allylic amination product in 80% yield and 56% enantiomeric excess, thus establishing the feasibility of dynamic kinetic resolution. [reaction: see text]
在4,5-二氯邻苯二甲酰亚胺存在下，将森田-贝利斯-希尔曼（MBH）乙酸酯暴露于叔膦催化剂中，可通过串联S(N)2'-S(N)2'机理实现区域特异性烯丙基取代。通过使用手性膦催化剂（R）-Cl-MeO-BIPHEP，手性外消旋MBH乙酸酯4以80%的产率和56%的对映体过量转化为相应的烯丙基胺化产物，从而确立了动态动力学拆分的可行性。[反应：见正文]
