Takasago International Corporation

Akifumi Yoshida

Takashi Miura

Toshiyuki Murayama

Toyohiko Kobayashi

Hidenori Kumobayashi

Noboru Sayo

Takao Saito

Kazuhiko Matsumura

Tohru Yokozawa

Wataru Kuriyama

Xiaoyong Zhang

Yasunori Ino

Tatsuya Ohmoto

A method for producing alcohols which comprises reducing esters or lactones with hydrogen gas in the presence of a catalyst comprising (i) a ruthenium compound, (ii) a monodentate monophosphine or a bidentate bisphosphine, and (iii) an amine. Examples of the catalyst include a ruthenium (Ru) complex represented by the formula:RuXX(L)(L)[Xand Xeach represent an anionic ligand, Lrepresents a phosphine ligand, m is 1 when Lis bidentate, while m is 2 when Lis monodentate, Lrepresents an amine ligand, and n is 1 when Lis bidentate, while n is 2 when Lis monodentate.] and a catalyst comprising an amine and a ruthenium (Ru) complex of the formula: RuXX(L)[Lrepresents a monophosphine ligand and r is 3 or 4.].

Method for producing alcohols

A phosphine-phosphinite compound represented by formula (I): ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, and a process for preparing a 4-�(R)-1'-formylethyl!azetidin-2-one derivative using the compound (I). The compound (I), either in combination, or as a complex, with a transition metal compound, is useful as a catalyst for asymmetric hydroformylation and makes it possible to easily synthesize an important intermediate for carbapenem antibiotics or a precursor thereof at high regioselectivity and diastereo-selectivity.

Phospphine-phosinite compound and process for preparing

The present invention provides a method for producing novel optically active diphosphine compounds �2,2'-bis(di-substituted phosphino)-1,1'-binaphthyl compounds! having a selectivity (chemoselectivity or enantioselectivity) and catalytic activity different from those of conventional BINAP compounds. In a method of the present invention for producing an optically active diphosphine compound (i.e., 2,2-bis(di-substituted phosphino)-1,1'-binaphthyl), 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl is reacted, in the presence of a transition metal-phosphine complex, with a phosphineoxide compound represented by the following general formula:

Method for producing optically active diphosphine compounds

A process for preferentially producing a 4-(1-carboxyalkyl) azetidin-2-one derivative represented by formula (II.beta.): ##STR1## wherein R.sup.3 represents a lower alkyl group and R.sup.4 represents a hydrogen atom or a hydroxy-protective group, which involves deesterifying and decarboxylating a 4-(1,1-dialkoxycarbonylalkyl) azetidin-2-one derivative represented by formula (I): ##STR2## wherein R.sup.1 and R.sup.2 are identical or different and each represents an alkyl group, an alkenyl group, or an aralkyl group, R.sup.3 and R.sup.4 each has the meaning as defined above, and R.sup.5 represents an amino-protective group, and after that, eliminating the amino-protective group from the derivative, where the 4-(1-carboxyalkyl)azetidin-2-one derivative of formula (II.beta.) is present in an amount of at least 61% by mol of all 4-(1-carboxyalkyl)azetidin-2-one derivatives produced.

4-(1,1-dialkoxycarbonylalkyl) azetidin-2-one derivative and process for

A 4-(1,1-dialkoxycarbonylalkyl )azetidin-2-one derivative represented by formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and each represents an alkyl group, an alkenyl group, or an aralkyl group, R.sup.3 represents a lower alkyl group, R.sup.4 represents a hydrogen atom or a hydroxyl-protective group, and R.sup.5 represents a hydrogen atom or an amino-protective group, and a process for producing a 4-(1-carboxyalkyl)azetidin-2-one derivative represented by formula (II) useful as an intermediate for 1.beta.-alkylcarbapenem-type antibacterials: ##STR2## wherein R.sup.3 represents a lower alkyl group and R.sup.4 represents a hydrogen atom or a hydroxyl-protective group, which comprises de-esterifying and decarboxylating the derivative represented by formula (I), and in the case where an amino-protective group is present in the derivative of formula (I), eliminating the protective group from the derivative, are disclosed.

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Kanagawa, Japan

Akifumi Yoshida