To obtain only one enantiomer of the subject compound useful as an intermediate for medicines, etc., by a new method without using a nonefficient optical resolution method, by using binaphthol moniether-tin tetrachloride complex.
3,4-Bistrimethylsilyloxytricyclo[4.2.1.02.5]nona-3,7-diene of formula I (TMS is trimethylsilyl) as a starting substance is reacted with a binaphthol monoether-tin tetrachloride complex of formula II or formula III (R is a straight- chain alkyl, aryl or the like) to give the objective compound of formula IV or formula V. A compound in which R is isopropyl, an aryl or the like in the complex of formula II or formula III is a new compound and is obtained by adding an azodicarboxylic acid diester to one of optically active binaphthols of formula VI and formula VII, an alcohol of the formula R-OH and triphenylphosphine to give a binaphthol monoether and reacting the binaphthol monoether with tin tetrachloride.
TANIGUCHI TAKAHIKO