Highly Effective Configurational Assignment Using Bisthioureas as Chiral Solvating Agents in the Presence of DABCO

被引：44

作者：

Bian, Guangling ^{[1
]}

Fan, Hongjun ^{[2
]}

Huang, Huayin ^{[1
]}

Yang, Shiwei ^{[1
]}

Zong, Hua ^{[1
]}

Song, Ling ^{[1
]}

Yang, Genjin ^{[3
]}

机构：

[1] Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China

[3] Second Mil Med Univ, Sch Pharm, Shanghai 200433, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 06期

关键词：

ABSOLUTE-CONFIGURATION; NMR; CYANOHYDRINS;

D O I：

10.1021/acs.orglett.5b00030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly effective H-1 NMR method for determining the absolute configurations of various chiral a-hydroxyl acids and their derivatives has been developed with the use of bisthioureas (R)-CSA 1 and (S)-CSA 1 as chiral solvating agents in the presence of DABCO, giving distinguishable proton signals with up to 0.66 ppm chemical shift nonequivalence. Computational modeling studies were performed with Gaussian09 to reveal the chiral recognition mechanism.

引用

页码：1369 / 1372

页数：4

共 21 条

[1] A LINK BETWEEN MACROSCOPIC PHENOMENA AND MOLECULAR CHIRALITY - CRYSTALS AS PROBES FOR THE DIRECT ASSIGNMENT OF ABSOLUTE-CONFIGURATION OF CHIRAL MOLECULES [J].