Recent developments in Cope-type hydroamination reactions of hydroxylamine and hydrazine derivatives.
Cope-type hydroaminations are versatile for the direct amination of alkenes, alkynes and allenes using hydroxylamines and hydrazine derivatives. These reactions occur via a concerted, 5-membered cyclic transition state that is the microscopic reverse of the Cope elimination. This article focuses on recent developments, including intermolecular variants, directed reactions, and asymmetric variants using aldehydes as tethering catalysts, and their applications in target-oriented synthesis.
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada. andre.beauchemin@uottawa.
André M
AM
Beauchemin
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D006834:Hydrazines / Q000737:chemistry*; D019811:Hydroxylamine / Q000737:chemistry*; D006898:Hydroxylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D000480:Alkynes; D006834:Hydrazines; D006898:Hydroxylamines; C029424:hydrazine; D019811:Hydroxylamine