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Stereoselective allylation of α-hydroxy aldimines and its application to the formal synthesis of (−)-β-conhydrine
Tetrahedron ( IF 2.1 ) Pub Date : 2017-12-13 , DOI: 10.1016/j.tet.2017.12.024
Yong-Taek Lee , Changyoung Jung , In-Soo Myeong , Sang-Hyun Lee , Jin-Seok Kim , Won-Hun Ham

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 addition to N-PMP-substituted α-hydroxy aldimine.



中文翻译:

α-羟基醛亚胺的立体选择性烯丙基化及其在(-)-β-conhydrine形式合成中的应用

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。

更新日期:2017-12-13
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