Synthesis of Imidates : TFA-Mediated Regioselective Amide Alkylation Using Meerwein's Reagent
(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.
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https://lup.lub.lu.se/record/dce8ca31-b406-4e82-ab71-b65165a44465
- author
- Popov, Kirill LU and Somfai, Peter LU
- organization
- publishing date
- 2016-04-15
- 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 (ACS)
- external identifiers
-
- pmid:27019206
- wos:000374436900048
- scopus:84966318845
- 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
- 2024-10-05 22:30:00
@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 (ACS)}}, 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}}, doi = {{10.1021/acs.joc.6b00424}}, volume = {{81}}, year = {{2016}}, }