Jump to main content
Jump to site search

Issue 4, 2019
Previous Article Next Article

The inverted ketene synthon: a double umpolung approach to enantioselective β2,3-amino amide synthesis

Author affiliations

Abstract

A stereocontrolled synthesis of β2,3-amino amides is reported. Innovation is encapsulated by the first use of nitroalkenes to achieve double umpolung in enantioselective β-amino amide synthesis. Step economy is also fulfilled by the use of Umpolung Amide Synthesis (UmAS) in the second step, delivering the amide product without intermediacy of a carboxylic acid or activated derivative. Molybdenum oxide-mediated hydride reduction provides the anti2,3-amino amide with high selectivity.

Graphical abstract: The inverted ketene synthon: a double umpolung approach to enantioselective β2,3-amino amide synthesis

Back to tab navigation

Supplementary files

Article information


Submitted
29 Sep 2018
Accepted
11 Nov 2018
First published
12 Nov 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 1138-1143
Article type
Edge Article

The inverted ketene synthon: a double umpolung approach to enantioselective β2,3-amino amide synthesis

M. Vishe and J. N. Johnston, Chem. Sci., 2019, 10, 1138
DOI: 10.1039/C8SC04330B

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements