Ionic liquid media resulted in the first asymmetric aminohalogenation reaction of alkenes.
[reaction: see text] The first asymmetric aminohalogenation of functionalized alkenes has been established. The ionic liquid [bmim][BF4] was found to be the only effective media for success as normal organic solvents failed to give any product for this reaction. The reaction is also very convenient to perform by simply mixing the three reactants, cinnamates, N,N-dichloro-p-toluenesulfonamide, and catalyst, together with 4 A molecular sieves at room temperature in [bmim][BF4] in any convenient vial of appropriate size without special protection from inert gases. Good chemical yields (60-72%) and diastereoselectivities (up to 75% de) have been obtained with a good scope of substrates. The resulting individual diastereomers have been cleanly separated via column chromatography. The absolute stereochemistry of the reaction was unambiguously determined by X-ray structural analysis.
Xu
Xin
X
Department of Chemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
Kotti
S R S Saibabu
SR
Liu
Junying
J
Cannon
John F
JF
Headley
Allan D
AD
Li
Guigen
G
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D018360:Crystallography, X-Ray; D006219:Halogens / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D000475:Alkenes; D006219:Halogens