The orthoester Johnson-Claisen rearrangement of allylic terpenols in the presence of acidic ionic liquid

被引：5

作者：

Kryshtal, Galina V. ^{[1
]}

Zhdankina, Galina M. ^{[1
]}

Ignat'ev, Nikolai V. ^{[2
]}

Schulte, Michael ^{[2
]}

Zlotin, Sergei G. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

[2] Merck KGaA, Frankfurter Str 250, D-64293 Darmstadt, Germany

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2016年 / 183卷

关键词：

Johnson-Claisen rearrangement; Terpenols; Ionic liquids; Reusable catalyst; EFFICIENT; ACETALIZATION; ALKYLATION; PROTECTION; CARBONYLS; CATALYSTS; ESTERS; NEROL;

D O I：

10.1016/j.jfluchem.2016.01.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A convenient protocol for the synthesis of natural isoprenoid-derived carboxylic esters via reaction of allylic terpenols with triethyl orthoacetate (propionate) in the presence of 1-butyl-3-methylimidazolium hexafluorophosphate, [bmim][PF6] (10 mol%), has been developed. The desired terpene derivatives were prepared in moderate to high yield. The ionic liquid (IL) can be easily separated from the products and repeatedly used up to ten times without reduction in the product yield. Experimental data evidence that HF, generated in situ from the IL, most likely acts as a true catalyst in the Johnson-Claisen rearrangement. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：23 / 29

页数：7

共 50 条

[1] Total synthesis of (±)-halomon by a Johnson-Claisen rearrangement
Schlama, T
Baati, R
Gouverneur, V
Valleix, A
Falck, JR
Mioskowski, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (15) : 2085 - 2087
[2] Exopericyclic stereocontrol in Johnson-Claisen rearrangements of allylic sulfides
Craig, Donald
Harvey, John W.
O'Brien, Alexander G.
White, Andrew J. P.
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (37) : 6932 - 6934
[3] Synthesis of bisabolane sesquiterpenes:A Johnson-Claisen rearrangement approach
Zhen Ting Du~(a
[J]. Chinese Chemical Letters, 2010, 21 (07) : 813 - 815
[4] The Orthoester Johnson-Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates-Recent Advances
Fernandes, Rodney A.
Chowdhury, Asim K.
Kattanguru, Pullaiah
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (14) : 2833 - 2871
[5] Synthetic studies towards the anti-inflammatory agent, oleocanthal using a Johnson-Claisen (orthoester) rearrangement strategy
Kueh, Jui Thiang Brian
O'Connor, Patrick D.
Huegel, Helmut
Brimble, Margaret A.
[J]. ARKIVOC, 2009, : 58 - 71
[6] Synthesis of halomon via Johnson-Claisen rearrangement.
Schlama, T
Gouveneur, V
Valleix, A
Falck, JR
Mioskowski, C
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U108 - U108
[7] Synthesis of bisabolane sesquiterpenes: A Johnson-Claisen rearrangement approach
Du, Zhen Ting
Yu, Hong Rui
Xu, Yan
Li, Yong
Li, An Pai
[J]. CHINESE CHEMICAL LETTERS, 2010, 21 (07) : 813 - 815
[8] A Synthesis of (-)-(R)- and (+)-(S)-Lavandulol, (+)-Lavandulyl 2-Methylbutanoate, and (+)-Lavandulyl Senecioate through Orthoester Johnson-Claisen Rearrangement
Fernandes, Rodney A.
Chowdhury, Asim K.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (23) : 5165 - 5170
[9] A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement
Saied, M'hamed
Gatri, Rafik
Al-Ayed, Abdullah Sulaiman
Arfaoui, Youssef
El Gaied, Mohamed Moncef
[J]. LETTERS IN ORGANIC CHEMISTRY, 2017, 14 (03) : 181 - 185
[10] Investigation of substituent effect on the Johnson-Claisen rearrangement: A DFT approach
Ghadari, Rahim
Shaabani, Ahmad
[J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2010, 961 (1-3): : 83 - 87

← 1 2 3 4 5 →