Advanced

Synthesis of Imidates : TFA-Mediated Regioselective Amide Alkylation Using Meerwein's Reagent

Popov, Kirill LU and Somfai, Peter LU (2016) In Journal of Organic Chemistry 81(8). p.3470-3472
Abstract

Regioselective O-alkylation of an amide to form the corresponding imidate is a common synthetic problem, often resulting in varying amounts of N-alkylation. Screening existing methods for converting amides to imidates gave inconsistent or irreproducible results, sometimes affording N-alkylamide as the major product. A simple and reliable protocol for amide O-alkylation with complete regioselectivity has been designed, and its scope and efficiency demonstrated on a number of substrates.

Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
81
issue
8
pages
3 pages
publisher
The American Chemical Society
external identifiers
  • Scopus:84966318845
  • WOS:000374436900048
ISSN
0022-3263
DOI
10.1021/acs.joc.6b00424
language
English
LU publication?
yes
id
dce8ca31-b406-4e82-ab71-b65165a44465
date added to LUP
2016-06-23 08:30:22
date last changed
2017-01-01 08:28:50
@article{dce8ca31-b406-4e82-ab71-b65165a44465,
  abstract     = {<p>Regioselective O-alkylation of an amide to form the corresponding imidate is a common synthetic problem, often resulting in varying amounts of N-alkylation. Screening existing methods for converting amides to imidates gave inconsistent or irreproducible results, sometimes affording N-alkylamide as the major product. A simple and reliable protocol for amide O-alkylation with complete regioselectivity has been designed, and its scope and efficiency demonstrated on a number of substrates.</p>},
  author       = {Popov, Kirill and Somfai, Peter},
  issn         = {0022-3263},
  language     = {eng},
  month        = {04},
  number       = {8},
  pages        = {3470--3472},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {Synthesis of Imidates : TFA-Mediated Regioselective Amide Alkylation Using Meerwein's Reagent},
  url          = {http://dx.doi.org/10.1021/acs.joc.6b00424},
  volume       = {81},
  year         = {2016},
}