Catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water.
[reaction: see text] An operationally simple and environmentally benign protocol for the catalytic asymmetric ring opening of meso-epoxides with aromatic amines has been developed. The reactions proceeded smoothly in the presence of 1 mol % of Sc(OSO3C12H25)3 and 1.2 mol % of a chiral bipyridine ligand in water to afford beta-amino alcohols in high yields with excellent enantioselectivities.
Azoulay
Stéphane
S
Graduate School of Pharmaceutical Sciences, University of Tokyo, HFRE Division, ERATO, Japan Science and Technology Agency, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Manabe
Kei
K
Kobayashi
Shü
S
D000588:Amines / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D000588:Amines; D000605:Amino Alcohols; D004852:Epoxy Compounds; D008698:Mesylates; C436603:scandium triflate; D014867:Water; D012538:Scandium