Stereoselective allylation of α-hydroxy aldimines and its application to the formal synthesis of (−)-β-conhydrine
作者:Yong-Taek Lee、Changyoung Jung、In-Soo Myeong、Sang-Hyun Lee、Jin-Seok Kim、Won-Hun Ham
DOI:10.1016/j.tet.2017.12.024
日期:2018.1
Stereoselective allylation of N-p-methoxyphenyl (PMP)-substituted α-hydroxy aldimines is described. Several Lewis acids (BF3·OEt2, SnCl4, TiCl4, ZnCl2, and MgBr2·OEt2) were employed to mediate the allylation reactions. The addition of the allyl group generates a new stereocenter and affords the syn vicinal amino alcohol. Formal synthesis of (−)-β-conhydrine (1) was accomplished via syn-selective allyl
的立体选择性烯丙基化ñ - p -甲氧基苯基(PMP) -取代的α羟基醛亚胺进行说明。几种路易斯酸(BF 3 ·OEt 2,SnCl 4,TiCl 4,ZnCl 2和MgBr 2 ·OEt 2)被用来介导烯丙基化反应。加入烯丙基生成新的立体中心和,得到顺式的连位氨基醇。(-)-β-conhydrine(1)的形式合成是通过将N -PMP取代的α-羟基醛亚胺进行顺-选择性烯丙基加成而完成的。