Peptide-catalyzed 1,4-Addition Reactions of Aldehydes to Nitroolefins

Authors

  • Robert Kastl ETH Zürich, Laboratorium für Organische Chemie, Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland
  • Yukihiro Arakawa ETH Zürich, Laboratorium für Organische Chemie, Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland
  • Jörg Duschmalé ETH Zürich, Laboratorium für Organische Chemie, Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland
  • Markus Wiesner ETH Zürich, Laboratorium für Organische Chemie, Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland
  • Helma Wennemers ETH Zürich, Laboratorium für Organische Chemie, Wolfgang-Pauli-Str. 10, CH-8093 Zürich, Switzerland. wennemers@org.chem.ethz.ch

DOI:

https://doi.org/10.2533/chimia.2013.279

Keywords:

Asymmetric catalysis, Conjugate addition reaction, Nitroolefins, Organocatalysis, Peptides

Abstract

Conjugate addition reactions of aldehydes to nitroolefins provide synthetically useful ?-nitroaldehydes. Here we summarize our research on peptide-catalyzed conjugate addition reactions of aldehydes to differently substituted nitroolefins. We show that peptides of the general type Pro-Pro-Xaa (Xaa = acidic amino acid) are not only highly active, robust and stereoselective catalysts but have also remarkable chemoselectivities.
CHIMIA Vol. 67 No. 4(2013): Laureates: Awards and Honors, SCS Fall Meeting 2012

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Published

2013-04-24

Issue

Vol. 67 No. 4 (2013): Laureates: Awards and Honors, SCS Fall Meeting 2012

Section

Scientific Articles

License

Copyright (c) 2013 Swiss Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

How to Cite

[1]
Chimia 2013, 67, 279, DOI: 10.2533/chimia.2013.279.