Dioxaphosphorinanes, their preparation and use for resolving optically active compounds

A method for preparing optically active isomers of dioxaphosphorinanes comprising:

• (a) reacting the corresponding racemate of one of the optically active dioxaphosphorinanes of the general formula:
• ##STR5## wherein, M represents a hydrogen atom, a metal ion or an ammonium ion;
• R1 and R2, individually, represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms or a nitro group or, together, represent a methylene dioxy group;
• and R3 and R4, individually, represents a halogen atom, an alkyl group having from 1 to 4 carbon atoms or a hydrogen atom so long as only one of the groups R3 and R4 represents a hydrogen atom or, together, represent a cyclohexyl group, in a solvent with an optically active amino-compound to form a diastereomeric salt which at least partially crystallizes out and a diastereomeric salt which remains in solution;
• (b) separating the crystallized-out salts from the dissolved salts;
• and
• (c) hydrolyzing one or both of the separated salts.

A method for preparing optically active isomers of dioxaphosphorinanes comprising:

• (a) reacting the corresponding racemate of one of the optically active dioxaphosphorinanes of the general formula:
• ##STR6## wherein, M represents a hydrogen atom, a metal ion or an ammonium ion;
• R1 and R2, individually, represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a nitro group or, together, represent a methylene dioxy group;
• and R3 and R4, individually, represents a halogen atom, an alkyl group having from 1 to 4 carbon atoms or a hydrogen atom so long as only one of the groups R3 and R4 represents a hydrogen atom or, together, represent a cyclohexyl group, in a solvent with an optically active amino-compound selected from the group consisting of (-)-ephedrine, (+)-2-amino-1-phenyl-1,3-propanediol, (-)-2-amino-1-butanol and (-)-para-hydroxyphenylglycine to form a diastereomeric salt which at least partially crystallizes out and a diastereomeric salt which remains in solution;
• (b) separating the crystallized-out salts from the dissolved salts;
• and
• (c) hydrolyzing one or both of the separated salts.

A method for separating an optically active isomer of an amino-compound from its corresponding racemate using a dioxaphosphorinane comprising:

• (a) reacting the racemate with an optically active dioxaphosphorinane of the general formula:
• ##STR7## wherein, M represents a hydrogen atom, a metal ion or an ammonium ion;
• R1 and R2, individually, represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms or a nitro group or, together, represent a methylene dioxy group;
• and R3 and R4, individually, represents a halogen atom, an alkyl group having from 1 to 4 carbon atoms or a hydrogen atom so long as only one of the groups R3 and R4 represents a hydrogen atom or, together, represent a cyclohexyl group, to form a diasteromeric salt which crystallizes out and a diasteromeric salt which remains in solution and
• (b) separating the two salts from one another.