Literature DB >> 26883782

Lewis Acid Triggered Regioselective Magnesiation and Zincation of Uracils, Uridines, and Cytidines.

Lydia Klier1, Eider Aranzamendi1, Dorothée Ziegler1, Johannes Nickel1, Konstantin Karaghiosoff1, Thomas Carell1, Paul Knochel1.   

Abstract

The Lewis acid MgCl2 allows control of the metalation regioselectivity of uracils and uridines. In the absence of the Lewis acid, metalation of uracil and uridine derivatives with TMPMgCl·LiCl occurs at the position C(5). In the presence of MgCl2, zincation using TMP2Zn·2LiCl·2MgCl2 occurs at the position C(6). This metalation method provides easy access to functionalized uracils and uridines. Using TMP2Zn·2LiCl·2MgCl2 also allows to functionalize cytidine derivatives at the position C(6).

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Year:  2016        PMID: 26883782     DOI: 10.1021/acs.orglett.6b00190

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Enzymatic synthesis of nucleoside analogues from uridines and vinyl esters in a continuous-flow microreactor.

Authors:  Li-Hua Du; Jia-Hong Shen; Zhen Dong; Na-Ni Zhou; Bing-Zhuo Cheng; Zhi-Min Ou; Xi-Ping Luo
Journal:  RSC Adv       Date:  2018-04-03       Impact factor: 4.036

2.  Regioselective Magnesiation and Zincation Reactions of Aromatics and Heterocycles Triggered by Lewis Acids.

Authors:  Alexander Kremsmair; Andreas Hess; Benjamin Heinz; Paul Knochel
Journal:  Chemistry       Date:  2021-11-29       Impact factor: 5.020

3.  Preparation of Primary and Secondary Dialkylmagnesiums by a Radical I/Mg-Exchange Reaction Using sBu2 Mg in Toluene.

Authors:  Alisa S Sunagatullina; Ferdinand H Lutter; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-09       Impact factor: 16.823

  3 in total

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