Tokyo Institute of Technology

Central Glass Company, Limited

Kohsuke Aikawa

Koichi Mikami

Akihiro Ishii

Takashi Ootsuka

Takashi Masuda

Kaori Mogi

Yuta Hioki

Misugi Kato

Junpei Aida

A method for producing an optically active fluorine-containing oxeten, the method being provided to include the steps of causing a fluorine-containing &#x3b1;-ketoester and an internal alkyne to react with each other in the presence of a transition metal complex that has an optically active ligand.

Method for producing optically active fluorine-containing oxeten

Disclosed is a method of producing an optically active fluorinated oxetane, which can be an important pharmaceutical or agricultural intermediate, by reaction of a fluorinated &#x3b1;-keto ester with an acyl alkenyl ether in the presence of a transition metal complex with an optically active ligand. This method utilizes a catalytic asymmetric synthesis process and does not require a stoichiometric amount of chiral source. It is thus possible to dramatically reduce the amount of use of the asymmetric catalyst especially when the reaction is performed at a high concentration of substrate (with the use of a small amount of reaction solvent) or in the absence of a reaction solvent (under neat conditions). Further, the target optically active fluorinated oxetane can be obtained with high yield and with very high optical purity. The product contains almost no difficult-to-separate impurity and shows high chemical purity.

Method for producing optically active fluorinated oxetane

An optically active, fluorine-containing carbonyl-ene product is produced by reacting a fluorine-containing &#x3b1;-ketoester with an alkene in the presence of a transition metal complex having an optically active ligand. There are Mode 1 of conducting this reaction in the absence of reaction solvent, Mode 2 of conducting this reaction in a solvent that is low in relative dielectric constant, and Mode 3 of conducting this reaction in a halogenated hydrocarbon-series solvent. In each of these three modes, it is possible to produce the optically active, fluorine-containing carbonyl-ene product with low cost.

Method for producing optically active fluorine-containing carbonyl-ene product

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Tokyo, Japan

Kohsuke Aikawa