Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes.
A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines were synthesized in good to excellent yields and diastereoselectivities.
Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, USA.
Fatima C
FC
Sequeira
Sherry R
SR
Chemler
D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D009025:Morpholines; D003300:Copper