A straightforward, one-pot protocol for the preparation of libraries of 2-oxazolines.
A practical protocol for the parallel synthesis of 2-oxazolines using polymer-supported reagents is described. Polymer-supported Mukaiyama reagent is used to couple a carboxylic acid with an amino alcohol, giving a beta-hydroxyamide, which is then cyclized in situ using either polymer-supported sulfonyl chloride resin or polymer-bound 2-fluoropyridinium triflate. Both 2,4-disubstituted and 2,4,5-trisubstituted 2-oxazolines are obtained in high yields and excellent purities after a simple resin filtration and solvent evaporation routine.
Crosignani
Stefano
S
Serono Pharmaceutical Research Institute, 14 Chemin des Aulx, 1228 Plan-les-Ouates, Geneva, Switzerland. stefano.crosignani@serono.com
Swinnen
Dominique
D
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014105:Tosyl Compounds / Q000737:chemistry
D000276:Adjuvants, Immunologic; D002264:Carboxylic Acids; D010080:Oxazoles; D014105:Tosyl Compounds