Proton-exchanged montmorillonite-mediated reactions of methoxybenzyl esters and ethers

被引：12
|
作者：
Chen, Dongyin [1 ,2 ]
Xu, Chang [1 ,2 ]
Deng, Jie [1 ,2 ]
Jiang, Chunhuan [1 ,2 ]
Wen, Xiaoan [1 ,2 ]
Kong, Lingyi [1 ,2 ]
Zhang, Ji [3 ]
Sun, Hongbin [1 ,2 ,3 ]
机构：
[1] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 210009, Peoples R China
[2] China Pharmaceut Univ, Ctr Drug Discovery, Nanjing 210009, Peoples R China
[3] China Pharmaceut Univ, Dept Phys Chem, Nanjing 210009, Peoples R China
来源：
TETRAHEDRON | 2014年 / 70卷 / 11期
关键词：
Proton-exchanged montmorillonite; Quinone methides; Benzylation reactions; p-Methoxybenzyl group; Deprotection; SELECTIVE DEPROTECTION; SUBSTITUTION-REACTIONS; CATALYZED BENZYLATION; NATURAL-PRODUCTS; PMB-ETHERS; EFFICIENT; MILD; DERIVATIVES; ALCOHOLS; MECHANISM;
D O I：
10.1016/j.tet.2014.01.064
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Proton-exchanged montmorillonite (H-mont) was found to be an eco-friendly and cost-effective catalyst for the generation of O-methylated quinone methides (QM) from the corresponding p or o-methoxybenzyl esters and ethers. Nucleophilic trapping of the O-methylated QM with arenes, alcohols, 1,3-dicarbonyl compounds, silyl enol ethers, and allylsilanes has been carried out, respectively, leading to eco-friendly benzylation reactions. Using this protocol, H-mont-mediated deprotection of PMB-protected esters and ethers have been realized for the first time. This work would pave the way for further exploration in O-alkylated QM that are of chemical and biological significance. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1975 / 1983
页数：9
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