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

Robert Kastl; Yukihiro Arakawa; Jörg Duschmalé; Markus Wiesner; Helma Wennemers

doi:10.2533/chimia.2013.279

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.