Japan Science and Technology Agency

Kaneka Corporation

Takasago International Corporation

Nagoya University

Susumu Saito

Hisashi Yamamoto

Norie Momiyama

Yuhei Yamamoto

Hiromi Torii

Ryoji Noyori

Kenji Inoue

Takaji Matsumoto

Kazuki Iida

Hirofumi Maeda

Izuru Nagasaki

Sunkook Lee

Santosh Agrawal

Sota Nimura

Katsuaki Toda

Yuki Takada

Masayuki Naruto

Takashi Miura

A hydrogen transfer reaction may be more efficiently promoted by using a metal complex represented by Formula (2):  More specifically, the metal complex enables a hydrogenation reaction of various substrates having a stable carbonyl group or the like to be advanced with a high yield under mild conditions.

Ligand, metal complex containing ligand, and reaction using metal complex containing ligand

The present invention is directed to a process of making &#x3b1;-aminooxyketone and &#x3b1;-hydroxyketone compounds. The synthetic pathway generally involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of the formula (IV): wherein X-Xrepresent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the &#x3b1;-aminooxyketone compound formed to the &#x3b1;-hydroxyketone compound. The present invention results in &#x3b1;-aminooxyketone and &#x3b1;-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol/Michael reaction. The substrates of this reaction are generally cyclic &#x3b1;,&#x3b2;-unsaturated ketone substrate and a nitroso substrate. This methodology generally involves reacting the cyclic &#x3b1;,&#x3b2;-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.

Process of making &#x3b1;-aminooxyketone/&#x3b1;-aminooxyaldehyde and &#x3b1;-hydroxyketone/&#x3b1;-hydroxyaldehyde compounds and a process of making reaction products from cyclic &#x3b1;, &#x3b2;-unsaturated ketone substrates and nitroso substrates

The present invention is directed to a process of making &#x3b1;-aminooxyketone and &#x3b1;-hydroxyketone compounds. The synthetic pathway generally involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of the formula (IV): wherein X&#x2014;Xrepresent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the &#x3b1;-aminooxyketone compound formed to the &#x3b1;-hydroxyketone compound. The present invention results in &#x3b1;-aminooxyketone and &#x3b1;-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol/Michael reaction. The substrates of this reaction are generally cyclic &#x3b1;,&#x3b2;-unsaturated ketone substrate and a nitroso substrate. This methodology generally involves reacting the cyclic &#x3b1;,&#x3b2;-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.

Process of making alpha-aminooxyketone/alpha-aminooxyaldehyde and alpha-hydroxyketone/alpha-hydroxyaldehyde compounds and a process making reaction products from cyclic alpha, beta-unsaturated ketone substrates and nitroso substrates

Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein Rrepresents a spacer; R, R, R, R, Rand Rindependently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R, R, R, R, Rand Rindependently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.

Method for producing alcohol by hydrogenating lactone and carboxylic acid ester in liquid phase

The present invention is directed to a process of making &#x3b1;-aminooxyketone and &#x3b1;-hydroxyketone compounds. The synthetic pathway involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of the formula (IV): wherein X-Xrepresent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the &#x3b1;-aminooxyketone compound formed to the &#x3b1;-hydroxyketone compound which results in &#x3b1;-aminooxyketone and &#x3b1;-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol/Michael reaction involving a cyclic &#x3b1;,&#x3b2;-unsaturated ketone substrate and a nitroso substrate. This methodology involves reacting the cyclic &#x3b1;,&#x3b2;-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.

Process of making &#x3b1;-aminooxyketone/&#x3b1;-aminooxyaldehyde and &#x3b1;-hydroxyketone/&#x3b1;-hydroxyaldehyde compounds and a process making reaction products from cyclic &#x3b1;,&#x3b2;-unsaturated ketone substrates and nitroso substrates

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Nagoya, Japan

Susumu Saito