The present invention relates to the field of chemical processes and, more particularly, it concerns valuable new chemical intermediates of formula (IV) for producing perfuming ingredients.

The present invention relates to the field of chemical processes and, more particularly, it concerns valuable new chemical intermediates of formula (IV) for producing perfuming ingredients.

The present invention relates to the field of chemical processes and, more particularly, it concerns valuable new chemical intermediates of formula (IV) for producing perfuming ingredients.

A method for producing an organometallic nucleophile includes reacting an organohalide and a metal or metal compound with each other by a mechanochemical process in the presence of an ether compound in an amount of 0.5 to 10.0 equivalents relative to 1 equivalent of the organohalide. By utilizing the method, a method for producing an organometallic nucleophile can be performed without using a large-scale apparatus, a reaction method for reactions between an organometallic nucleophile and various organic electrophiles can be performed by an efficient and simplified means, and a simplified method for producing an organometallic nucleophile can be performed with high reactivity.

A method for producing an organometallic nucleophile includes reacting an organohalide and a metal or metal compound with each other by a mechanochemical process in the presence of an ether compound in an amount of 0.5 to 10.0 equivalents relative to 1 equivalent of the organohalide. By utilizing the method, a method for producing an organometallic nucleophile can be performed without using a large-scale apparatus, a reaction method for reactions between an organometallic nucleophile and various organic electrophiles can be performed by an efficient and simplified means, and a simplified method for producing an organometallic nucleophile can be performed with high reactivity.

The invention comprises novel chiral metal complex compounds of the formula ##STR00001## wherein M, PR.sup.2, R.sup.3 and R.sup.4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.

The invention comprises novel chiral metal complex compounds of the formula ##STR00001## wherein M, PR.sup.2, R.sup.3 and R.sup.4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.

A compound of general formula (I-1): ##STR00001## wherein the symbols are defined in the specification, has a selective S1P.sub.5 receptor binding activity and modulates the function of an S1P.sub.5 receptor, and can therefore be a therapeutic agent for a S1P.sub.5-mediated disease, for example, neurodegenerative diseases such as schizophrenia, Binswanger's disease and the like.

A compound of general formula (I-1): ##STR00001## wherein the symbols are defined in the specification, has a selective S1P.sub.5 receptor binding activity and modulates the function of an S1P.sub.5 receptor, and can therefore be a therapeutic agent for a S1P.sub.5-mediated disease, for example, neurodegenerative diseases such as schizophrenia, Binswanger's disease and the like.

The invention comprises novel chiral metal complex compounds of the formula

##STR00001##

wherein M, PR.sup.2, R.sup.3 and R.sup.4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.