Dioxaphosphorinanes, their preparation and use for resolving opt

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562401, 564303, 564304, C07F 921, C07B 5700

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active

048144770

ABSTRACT:
A new family of compounds known as dioxaphosphorinanes having the formula: ##STR1## 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.
A method for preparing these dioxaphosphorinanes by reacting phosphoryl chloride with a substituted 1-phenyl-1,3-dihydroxypropane is described. Also described is a method for resolving the new dioxaphosphorinanes into their optical isomers by reacting them with an optically active amino-compound. Similarly, a method for resolving the racemates of several amino-compounds, such as hydroxyphenylglycine and phenylalanine, into optically active isomers by reacting with a dioxaphosphorinane is described.

REFERENCES:
Kainosho et al., "Bull. of the Chemical Society of Japan," vol. 42, (1969) pp. 1713-1717.
Matrosov et al., "Chem. Abst.", vol. 85, (1976) 85:20188a.
Cram et al., "Organic Chemistry," (1964) Second Editions, pp. 162-175.
Majoral et al., "Chem Abst.," vol. 69,(1968) 26898y.

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