Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis.
Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis.
复制标题
DOI：
10.1021/jo400354r
复制
发表时间：
2013-04-19
期刊：
影响因子：
--
通讯作者：
Li G
中科院分区：
文献类型：
--
作者：
Pindi S;Wu J;Li G
设计合成了一种新的手性（Rs）-2-苯基-2-丙基亚磺酰胺，并将其衍生的醛亚胺和酮亚胺与烯丙基溴化镁进行了不对称加成反应。该反应在室温下方便地进行，以高产率（高达定量）和非对映选择性（高达> 99%de）得到一系列高烯丙基胺。通过依赖于基团辅助纯化（GAP）化学来获得纯产物，以避免传统的柱层析或重结晶纯化方法。二硫化物向（Rs）-硫代亚磺酸酯的转化也被证实是差距化学，其中洗涤粗产物可以产生纯的对映体。通过X射线分析确定了其绝对立体化学。
A new chiral (Rs)-2-phenyl-2-propyl sulfinamide has been designed and synthesized; its derived aldimines and ketimines have been applied for asymmetric addition reaction with allylmagnesium bromide. The reaction was conveniently performed at room temperature to give a series of homoallylic amines in high yields (up to quant) and diastereoselectivity (up to >99 % de). The pure products were obtained by relying on Group-Assisted Purification (GAP) chemistry to avoid traditional purification methods of column chromatography or recrystallization. The conversion of disulfide to (Rs)-thiosulfinate was also confirmed to be of the GAP chemistry in which washing crude product can generate pure enantiomer. The absolute stereochemistry has been determined by X-ray analysis.
登录
查看更多内容
影响因子：
3.6
作者：
Kattamuri, Padmanabha V.;Ai, Teng;Pindi, Suresh;Sun, Yinwei;Gu, Peng;Shi, Min;Li, Guigen
通讯作者：
Li, Guigen
影响因子：
3
作者：
Kaur P;Wever W;Rajale T;Li G
通讯作者：
Li G
影响因子：
9.8
作者：
Kaur, Parminder;Wever, Walter;Li, Guigen
通讯作者：
Li, Guigen
影响因子：
2.8
作者：
Francesco, Irene Notar;Egloff, Coraline;Colobert, Francoise
通讯作者：
Colobert, Francoise
影响因子：
3.6
作者：
Davis, FA;Reddy, RE;Carroll, PJ
通讯作者：
Carroll, PJ