Peptide catalyzed asymmetric conjugate addition reactions of aldehydes to nitroethylene--a convenient entry into gamma2-amino acids.
The peptide H-D-Pro-Pro-Glu-NH2 is a highly effective catalyst for conjugate addition reactions between aldehydes and nitroethylene. Only 1 mol % of H-d-Pro-Pro-Glu-NH2 and a 1.5-fold excess of aldehyde with respect to nitroethylene suffice to obtain gamma-nitroaldehydes and, after reduction, monosubstituted gamma-nitroalcohols in excellent yields and optical purities. The products can be readily converted into gamma2-amino acids, thereby opening an effective direct entry into this important class of compounds.
Wiesner
Markus
M
Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
Revell
Jefferson D
JD
Tonazzi
Sandro
S
Wennemers
Helma
H
D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D018698:Glutamic Acid / Q000737:chemistry; D008956:Models, Chemical; D009574:Nitro Compounds / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000596:Amino Acids; D005030:Ethylenes; D009574:Nitro Compounds; D010455:Peptides; D018698:Glutamic Acid; D011392:Proline