NOVEL CHIRAL BIARYL BIS(OXAZOLINES)

Novel chiral biaryl bis(oxazoline) have been prepared through a compli mentary use of three synthetic methods. The method of choice is determ ined by the structure of the oxazoline. For bis(oxazolines) containing ethylene spacers between the aromatic ring and the oxazoline groups, a general alkylation procedure based on 2-methyl-2-oxazoline has been developed and found to give very good yields (75-87%) of the desired p roducts. Bis(oxazolines) with the oxazoline moiety attached directly t o the aromatic ring were prepared by Ullmann coupling of the appropria te bromoaryl oxazolines. Those containing oxymethylene spacers were pr epared by the standard method involving condensation of amino alcohols with the appropriate dicarboxylic acids (84%).