Al(OTf)(3)-mediated epoxide ring-opening reactions: toward piperazine-derived physiologically active products.
Al(OTf)(3) is a good catalyst for the ring opening of epoxides, forming beta-amino alcohols bearing the piperazine motif. Two different strategies were examined, where the glycidyl ether resided on one-half of the molecule or the other, allowing insight into a best-case approach for the ring-opening step. Each half of the molecule contained an heteroatom that could be used either to attach the glycidyl moiety or as the nucleophile in the ring-opening reaction, for the same set of reagents, allowing this approach.
Williams
D Bradley G
DB
Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park 2006, South Africa. bwilliams@uj.ac.za
Cullen
Adam
A
D000537:Aluminum Oxide / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry*; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry*
D000605:Amino Alcohols; D004852:Epoxy Compounds; D006845:Hydrocarbons, Fluorinated; D009942:Organometallic Compounds; D010879:Piperazines; D014105:Tosyl Compounds; D000537:Aluminum Oxide