PURPOSE: To simply and efficiently produce the subject compound by asymmetrically alkylating an aldehyde compound having an alkoxy group at the β position with a dialkyl zinc in the presence of an optically active amino alcohol compound as a catalyst.
CONSTITUTION: An aldehyde compound having an alkoxy group at the β position is dissolved in a solvent such as hexane or THF, mixed with an optically active compound of formula II (R, R' are H, aliphatic hydrocarbon, aromatic hydrocarbon, etc.; * exhibits an optically active carbon) (e.g. dibutyl norephedrine) and further with a dialkyl zinc (e.g. diethyl zinc), stirred at room temperature for 10-20hrs and subsequently mixed with 1N hydrochloric acid to stop the reaction, followed by extracting the reaction solution and drying the extract to provide the objective compound of formula III [R1 is hydrocarbon, trialkyl silyl of formula: R3R4R5Si (R3-R5 are alkyl); R2 is aliphatic hydrocarbon, cyclic aliphatic hydrocarbon, etc.] such as 5-benzyloxy-3-hexanol.