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Synthesis 2018; 50(22): 4383-4394
DOI: 10.1055/s-0037-1610215
DOI: 10.1055/s-0037-1610215
paper
Directed Zincation or Magnesiation of 2- and 4-Pyrones and Their Derivatives
We would like to thank the Ludwig-Maximilians-University Munich for financial support. We thank Albemarle Corporation for the generous gift of chemicals and the SFB749 for financial support.Further Information
Publication History
Received: 14 June 2018
Accepted after revision: 25 June 2018
Publication Date:
09 August 2018 (online)
Dedicated to Professor Scott Denmark on the occasion of his 65th birthday
Abstract
A regioselective magnesiation of the 2-pyrone scaffold was developed. Magnesiation of this heterocycle by using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by trapping reactions with electrophiles such as aldehydes, allylic bromides, acid chlorides, and aryl iodides provided functionalized 2-pyrones. Furthermore, methyl coumalate and 3,5-dibromo-2H-pyran-2-one were zincated by using TMPZnCl·LiCl to afford zincated heterocycles, which reacted with typical electrophiles. A second magnesiation at position C3 of the 2-pyrone scaffold was achieved by using TMPMgCl·LiCl. Also, the zincation of the 4-pyrone scaffold at position C2 is reported, leading to functionalized 4-pyrones.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610215.
- Supporting Information
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