Facile ring opening of 2,3-epoxy-steroids with aromatic amines in ionic liquids.
Efficient ring opening of steroidal 2,3-epoxides with stoichiometric amount of aromatic amines has been carried out using an ionic liquid ([bmim](+)[BF(4)](-)) both as solvent and catalyst. The reactions were completely regio- and stereoselective in each case. The aminoalcohol products have chair conformations in ring A. The ionic liquid-mediated ring opening can efficiently be carried out with aliphatic amines like morpholine as well.
Horváth
Anita
A
University of Veszprém, Department of Organic Chemistry and Research Group for Petrochemistry of the Hungarian Academy of Sciences, Veszprém, Hungary.
Skoda-Földes
Rita
R
Mahó
Sándor
S
Berente
Zoltán
Z
Kollár
László
L
D024322:Amino Acids, Aromatic / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis*; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D007477:Ions / Q000737:chemistry*; D007664:Ketosteroids / Q000138:chemical synthesis / Q000737:chemistry; D008954:Models, Biological; D008968:Molecular Conformation; D012997:Solvents / Q000737:chemistry*; D013260:Steroids, Heterocyclic / Q000737:chemistry*
D024322:Amino Acids, Aromatic; D000605:Amino Alcohols; D000814:Aniline Compounds; D007477:Ions; D007664:Ketosteroids; D012997:Solvents; D013260:Steroids, Heterocyclic; C021313:methylaniline