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

Org Lett. 2016 Mar 4;18(5):1068-71. doi: 10.1021/acs.orglett.6b00190. Epub 2016 Feb 17.

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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques
  • Cytidine / chemical synthesis
  • Cytidine / chemistry*
  • Lewis Acids / chemistry*
  • Magnesium Chloride / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Stereoisomerism
  • Uracil / chemical synthesis
  • Uracil / chemistry*
  • Uridine / chemical synthesis
  • Uridine / chemistry*
  • Zinc / chemistry

Substances

  • Lewis Acids
  • Organometallic Compounds
  • TMPMgCl.LiCl
  • Magnesium Chloride
  • Uracil
  • Cytidine
  • Zinc
  • Uridine