Chisso Corporation

Masayuki Sato

Chikara Kaneko

Masahiko Yamaguchi

Hiromichi Ogasawara

The present invention provides a novel &bgr;-diketone compound represented by formula (3):

&bgr;-diketone compounds &bgr;-diketone compounds coordinated to metal, method of organic synthesis with these, and catalyst

There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Provided are optically active 5,6-epoxyhexanoic acid esters and novel optically active 6-substituted tetrahydropyran-2-one derivatives. That is, optically active 6-chloromethyltetrahydropyran-2-one can be synthesized by lactonizing optically active 2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one to form optically active 6-chloromethyltetrahydropyran-2,4-dione; reacting the thus formed compound with hydrogen in the presence of a catalyst to obtain optically active 6-chloromethyl-4-hydroxytetrahydropyran-2-one; subjecting this compound to a dehydration reaction, thereby obtaining optically active 6-chloromethyldihydropyran-2-one; reacting this compound with hydrogen in the presence of a catalyst to form optically active 6-chloromethyltetrahydropyran-2-one; and then treating this compound under basic conditions to prepare an optically active 5,6-epoxyhexanoic acid ester represented by the formula (6) ##STR1## (wherein the symbol * represents an asymmetric carbon atom, and R is a methyl group or an ethyl group).

Optically active 2,2-dimethyl-1,3-dioxin-4-ones and method for preparing

There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Furthermore, a method for preparing an optically active compound comprises reacting a racemic 1,3-dioxin-4-one with vinylacetate in the presence of lipase to resolve the racemic compound into optically active compound represented by the formula (3) ##STR1## and an optically active compound represented by the formula (4) ##STR2## which is an antipode of the compound represented by the formula (3).

A process for producing 3-oxo-6-formyl-2-oxabicyclo[3.3.0]-6-octene useful as an intermediate for producing prostaglandins, via a few steps from raw materials which can be relatively easily prepared. The process comprises subjecting 2,2-dimethyl-1,3-dioxin-4-one and cis-2-cyclopenten-1,4-diol to addition reaction in a solvent, preferably under a photo-irradiation, removing the solvent from the reaction mixture, adding water to the resulting adducts and reacting the resulting mixture on heating.

Process for producing an aldehydelactone

A process for producing 1,3-dioxin-4-one derivatives having a lower alkyl group at 2-position and useful as a starting raw material for prostaglandins, with a high yield is provided, which process comprises reacting formyl Meldrum's acid with a lower aliphatic carbonyl compound of 2 to 4 carbon atoms in a solvent containing the carbonyl compound at 100.degree. to 120.degree. C., while portionwise adding the acid into the solvent, the total quantity of the acid added being 0.2 mol or less per liter of the solvent.

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Sendai, Japan

Masayuki Sato