| 摘要 |
PROBLEM TO BE SOLVED: To obtain a new compound useful as an asymmetrically synthetic reagent for industrially advantageously producing an optically active compound having high optical purity to provide the optically active compound in high selectivity and high yield. SOLUTION: This new compound is the one of formula I [R1 is an alkyl; R2 is an alkyl, an aryl or the like; R3 is an alkyl or a hydroxyalkyl; (*) shows the position of an asymmetric carbon] or a salt thereof, e.g. (5S)-2-[(1S)-1- phenylethylimino]-3-[(1S)-1-phenyletyl]-1,3-diazabicycle[3.3.0]octane. The compound of formula I is obtained by subjecting an amino group-protected optically active proline derivative of formula II and an optically active amine derivative of formula III to condensation through dehydration, deprotecting the obtained proline derivative, reducing the amide group of the product, reacting the reduced product with thiophosgene in the presence of a base to provide a bicyclic thiourea, halogenating the obtained thiourea to provide an iminium salt of formula IV (X is a halogen), reacting the iminium salt with a primary amine in the presence of a base.
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