Catalytic Stereospecific Substitution of Enantioenriched Allylic Alcohols with Sodium Sulfinates

被引：47
作者：
Ma, Xian-Tao [1 ]
Dai, Rui-Han [1 ]
Zhang, Juan [1 ]
Gu, Yonghong [1 ]
Tian, Shi-Kai [1 ]
机构：
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 14-15期
基金：
中国国家自然科学基金;
关键词：
alcohols; palladium; stereospecificity; substitution; sulfones; 1,3-CHIRALITY TRANSFER; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; BOND FORMATION; C-C; OXYPALLADATION; AMINES; STEREOCHEMISTRY; SULFONYLATION; INDUCTION;
D O I：
10.1002/adsc.201400187
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An unprecedented stereospecific substitution reaction of enantioenriched allylic alcohols with sodium sulfinates has been developed for the asymmetric synthesis of allylic sulfones with excellent ee. A range of highly enantioenriched allylic alcohols smoothly underwent palladium diacetate/racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthylcatalyzed substitution with sodium sulfinates to give structurally diverse a-chiral allylic sulfones in moderate to excellent yields with complete retention of configuration. This study paves the way for the direct stereospecific substitution of enantioenriched allylic alcohols with sulfur nucleophiles.
引用
收藏
页码：2984 / 2988
页数：5
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