Synthesis and characterization of monoaryl esters of L-tartaric acid and their process for fries rearrangement

被引：2

作者：

Khan, Sher Wali ^{[1
,2
]}

Zaidi, Javaid Hussain ^{[2
]}

Khan, Gul Shahzada ^{[1
]}

Rashid, Haroon Ur ^{[3
]}

Umar, Muhammad Naveed ^{[4
]}

Jan, Abdul Khaliq ^{[1
]}

Galan, Carman ^{[5
]}

Haddow, Mairi ^{[5
]}

机构：

[1] Shaheed BB Univ Sheringal, Dept Chem, Dir Upper, Kpk, Pakistan

[2] Quaid I Azam Univ, Dept Chem, Islamabad, Pakistan

[3] Sarhad Univ Sci & Informat Technol, Dept Chem, Peshawar, Kpk, Pakistan

[4] Univ Malakand, Dept Chem, Chakdara, Kpk, Pakistan

[5] Univ Bristol, Sch Chem, Bristol, Avon, England

来源：

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2015年 / 12卷 / 10期

关键词：

L-Tartaric acid; Protection; Monoaryl esters; Fries rearrangement; EFFICIENT ASYMMETRIC OXIDATION; SIMMONS-SMITH REACTION; ALLYLIC ALCOHOLS; ALLYLBORATION REACTION; CHIRAL AUXILIARY; COMPLEXES; SULFOXIDES; SULFIDES; ALDEHYDES; TARTRATE;

D O I：

10.1007/s13738-015-0657-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral protected monoaryl esters (2a-2h) were synthesized from monoester of l-tartaric acid, having two asymmetric centers and C2 axis of symmetry. l-tartaric acid was protected and partially hydrolyzed to give the corresponding monoester. Monoester upon treatment with different substituted phenols gave desired monoaryl esters (2a-2h). Fries rearrangement of monoaryl esters was then tried under various conditions by using different Lewis acids. All the compounds were purified and characterized by using spectroscopic techniques like IR, H-1-NMR, C-13-NMR, HRMS-ESI, and elemental analysis. The structure of compound 2e was obtained by X-ray crystallography.

引用

页码：1819 / 1827

页数：9

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