Collect. Czech. Chem. Commun. 1989, 54, 151-159

Determination of the absolute configuration of secondary alcohols by modified Horeau's method using HPLC

Aleš Svatoša, Irena Valterováa, Anna Fábryováb and Jan Vrkoča

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Prague Institute of Chemical Technology, 166 28 Prague 6


A method for determination of absolute configuration of secondary alcohols, based on a modified Horeau's method, has been developed. The ratio of (1R,2'S)- and (1R,2'R)-N-[1-(1-naphthyl)-ethyl]-2-phenylbutanamides (V and VI, respectively) was determined by HPLC on a straight phase. The method was tested on a series of steroid and terpene model compounds and was used in the determination of absolute configuration of 15-ripperten-3α-ol (XV), the defense substance of Nasutitermes nigriceps termites. The sensibility of the determination is 100 nmol of the alcohol.