Chisso Corporation

Nagase Co., Ltd.

Hokko Chemical Industry Co., Ltd.

Hiroaki Sasai

Masakatsu Shibasaki

Mamoru Fujita

Yasuo Urata

Takayoshi Arai

Yoshihiro Tahara

Optically active 1-substituted phenyl-2-nitro alcohol derivatives having the formula (1) and the process for producing thereof, and 1-substituted phenyl-2-amino alcohol derivatives having the formula (2) and the process for producing thereof from the optically active 1-substituted phenyl-2-nitro alcohol derivatives. From these nitro alcohols, pharmaceuticals such as (R)-albutamin and (R)-sarmeterol useful as a bronchodilator is obtained via optically active amino alcohols which are useful pharmaceutical intermediates.

Optically active nitro alcohol derivatives, optically active amino alcohol derivatives, and process for producing thereof

Optically active nitro alcohol derivatives, optically active amino alcohol derivatives, and process for preparing the same

A process for producing an asymmetric compound using a metal complex containing no rare earth metal element is disclosed. The process affords an optically active compound having high optical purity. Optically active binaphthol having the chemical formula and lithium aluminum hydride are reacted, or the optically active binaphthol, a dialkyl aluminum hydride, and a base containing an alkali metal (or a base containing alkaline earth metal) are reacted to prepare a metal complex comprising optically active binaphthol, aluminum, and alkali metal (or alkaline earth metal). This metal complex can be used as a catalyst to perform an asymmetric Michael reaction, an asymmetric phosphonylation reaction, or the like, to obtain, in a high yield, an asymmetric compound having high optical purity.

Process for the preparation of an asymmetric compound using a metal

Process for the preparation of optically active 1-aminophosphonic acid

Process for preparing asymmetric compound by using metal complex

The present invention provides a catalyst for asymmetric synthesis prepared from a dialkali metal salt of an optically active 2,2'-dihydroxy-1,1'-binaphthyl represented by the formula (I.sub.R) ##STR1## or the formula (I.sub.S) ##STR2## (wherein M is Li, K or Na), a lanthanum compound represented by LaX.sub.3 (X is F, Cl, Br, I, NO.sub.3 or CH.sub.3 CO.sub.2) and an alkali metal alkoxide or an alkali metal hydroxide represented by MOR or MOH (M is Li, K or Na, and R is isopropyl or t-butyl), respectively, in the presence of a water-containing solvent. The catalyst of the present invention is extremely valuable as a catalyst for asymmetric synthesis of an asymmetric nitroaldol reaction useful in the synthesis of a .beta.-hydroxynitro compound which is an important synthetic raw material for an optically active compound such as a medicine.

Catalyst for asymmetric synthesis

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Chiba, Japan

Hiroaki Sasai