To obtain a new compound useful as an asymmetric ligand in producing asymmetric cyclopropanecarboxylic acids by a short process in good yield from inexpensive raw materials by reacting olefins with diazoacetic acid esters in the presence of a copper salt.
This compound is represented by formula I [X is a substituent group of formula I or III (R1 and R2 are each an alkyl, an aralkyl, etc.; R3 is a substitutable aryl; R4 is hydroxyl or amino); R5 to R8 are each H, an aryl, etc., with the proviso that at least R5 and R6 are not same; * is an asymmetric carbon; (*) exhibits possibility of asymmetric carbon], e.g. (4R)-2-(2-hydroxy-2,2- diphenylethyl)-4-phenyloxazoline. The compound is obtained by reacitng 2methyloxazolines of formula IV with ketones of the formula, R1COR2, arylcarboxylic acid esters of the formula, R3COOR14 (R14 is an alkyl) or arylnitriles of the formula, R3CN in the presence of a strong base, preferably at -80°C to 0°C.
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YANAGAWA MASAO