Nissan Chemical Industries Limited

Canon Kabushiki Kaisha

Kazutaka Arai

Katsuaki Miyaji

Fumie Sato

Yoshio Ohara

Yasuhiro Takahashi

Hiroyuki Nohira

Yasuo Takakuwa

Toyoko Iizumi

Kazuo Yoshinaga

Hiroo Matsumoto

Yashio Takakuwa

Syuuzi Tsuchiya

Disclosed herein is an .alpha.-methylene-cyclopentanone derivative represented by the formula [I] below which is useful as an intermediate for pharmaceuticals and insecticides, especially prostaglandins. Also disclosed herein is a process for producing the derivative advantageously on an industrial scale. ##STR1## where X denotes (.alpha.-OZ, .beta.-H) or (.alpha.-H, .beta.-OZ), with Z representing a protecting group for the hydroxyl group; U denotes (.alpha.-H, .beta.-R.sup.1) or (.beta.-R.sup.1, .alpha.-H); R.sup.1 denotes ##STR2## where R.sup.2 denotes a protected hydroxyl group, a substituted or unsubstituted C.sub.1-15 alkyl group, a substituted or unsubstituted C.sub.2-15 alkenyl group, a substituted or unsubstituted C.sub.2-15 alkynyl group, or a substituted or unsubstituted C.sub.6-15 aryl group; Z' denotes a protecting group for the hydroxyl group; and k is 0 or 1).

.alpha.-methylenecyclopentanone derivative and process for producing the

The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.

Substituted cyclic ketones, substituted cyclic enones, and process for

Optical resolution of (.+-.)-2-(3-benzoyl)-phenylpropionic acid is attained effeciently in high yield by the use of a specific optically active amine which is represented by the general formula [I]: ##STR1## wherein R.sup.1 either stands for a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, or an isopropyl group or participates, as a divalent group, in forming a benzene ring in combination with two carbon atoms adjoining each other in a benzene ring to which the substituent, R.sup.1, is bonded, R.sup.2 stands for a lower alkyl group, a hydroxymethyl group, an .alpha.-hydroxybenzyl group, or a ##STR2## group (R.sup.3 standing for a hydrogen atom, a chlorine atom, a bromine atom, or a methyl group), n for 0 or 1, and * for the center of optical activity.

Process for optical resolution of (.+-.)-2-(3-benzoyl)-phenylpropionic

The present invention relates to substituted cyclopentanone and cylohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.

Substituted cyclic kentones, substituted cyclic enones

An optically active polymer comprises recurring units of the following formula: ##STR1## wherein l is an integer of 5-1000, n is an integer of 1-3, m is an integer of 2-20, and * denotes the location of an asymmetric center. The optically active polymer has a good mutual solubility with a low-molecular weight mesomorphic compound and is easily mixed with the latter to provide a uniform liquid crystal composition which shows ferroelectricity and better film formability and stability than the low-molecular weight mesamorphic compound alone.

Optically active polymer and liquid crystal composition containing same

A compound having the formula: ##STR1## wherein R is a hydroxyl-protecting group, X is a hydrogen atom, CO.sub.2 R' (wherein R' is a hydrogen atom or an alkyl group having from 1 to 7 carbon atoms, or CO.sub.2 R' is a salt of CO.sub.2 H), or a group of the formula: ##STR2## and when X is a hydrogen atom, Y is CO.sub.2 R' (wherein R' is as defined above) or a group of the formula: ##STR3## and when X is CO.sub.2 R' or the group of the formula (i), Y is a hydrogen atom.

Optically active bicyclo carboxylic acids and their derivatives

2-Phenylpropoionic acid ester of Formula (I): ##STR1## wherein R represents p-nitrophenyl group, .beta.-naphthyl group or 2-(.beta.-naphthyl)ethyl group. Optical resolution of the above is carried out by preferential crystallization by seeding either one of the optical isomers into a super-saturated solution of a racemic modification thereof or a mixture of the optical isomers thereof. The efficiency of the optical resolution can be increased by optional addition of a recemizing agent comprising a strongly basic amine or an alcholate.

2-phenylpropionic acid esters, method for optical resolution thereof and

A process for preparing d-.alpha.-(6-methoxy-2-naphthyl)propionic acid, which comprises hydrolyzing an ester of d-.alpha.-(6-methoxy-2-naphthyl)propionic acid in an aqueous solution containing a basic catalyst.

Process for preparing D-.alpha.-(6-methoxy-2-naphtyl) propionic acid

A method for the preparation of an ester of .alpha.-thio-.alpha.-aromatic propionic acid derivatives of the formula: ##STR1## wherein R.sup.1 is alkyl, phenyl or benzothiazolyl, R.sup.2 is alkyl and Ar is an aromatic substituent. The method comprises reacting an ester of .alpha.-chloro-.alpha.-thiopropionic acid of the formula: ##STR2## with an aromatic compound of the formula ARH, in the presence of a Lewis acid. The method provides good reactivity and positional selectivity in the Friedel-Crafts reaction. Many esters of the formula (2) are useful as pharmaceuticals, agricultural chemicals, perfumes or their intermediates.

Method of preparing .alpha.-aromatic propionic acids and intermediates

Disclosed is a process for preparing an optical active alkyl ester of .alpha.-(6-methoxynaphth-2-yl)propionic acid from the racemic modification thereof or from a mixture of the optical isomers thereof by preferential crystallization. The efficiency of the optical resolution can be increased by adding a base which facilitates the racemization. The process comprises dissolving the racemic modification or the optical isomers in an organic solvent such as methanol, ethanol, etc., with or without a base such as sodium methoxide, sodium ethoxide, etc., and seeding seed crystals of one of the optical isomers to effect crystallization for optical resolution.

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Funabashi, Japan

Kazutaka Arai