Hoffmann-la Roche Inc.

Ciba-geigy Corporation

Roche Vitamins Inc.

Rolic Ag

Emil A Broger

Yvo Crameri

Rudolf Schmid

Marco Cereghetti

Bernd Heiser

Erich Widmer

Richard Buchecker

Michelangelo Scalone

Frank Kienzle

Christof Wehrli

Albert Pfiffner

Werner Hofheinz

Ulrich Zutter

Teodor Lukac

Reinhard Zell

Martin Karpf

Joseph Foricher

Hans G Leuenberger

Hans P Isenring

Theodor Siegfried

Marquard Imfeld

Alain Rageot

Arthur Meili

Robert K M Uller

Francedillaois Montavon

Dieter Bartoldus

Novel, chiral diarsine compounds, which are present in the (R)- or (S)- or (rac)-form, of the formula ##STR1## wherein R signifies an optionally substituted aryl from the group of phenyI, naphthyl, furyl and thienyl; C.sub.3-8 -cycloalkyl or C.sub.1-8 -alkyl;

Chiral diarsine compounds

A process for the manufacture of optically active (R)- or (S)-1-(4-methoxy-benzyl)-1,2,3,4,5,6,7,8-octahydro-isoquinoline adducts of the formula ##STR1## wherein HX signifies a mineral acid from the group of HBF.sub.4, H.sub.2 SO.sub.4, HPF.sub.6, HBr, HI, HCl,

Process for manufacture of optically active isochinole compounds

Optically active .alpha.-bromo- or .alpha.-chlorocarboxylic compounds of the formula ##STR1## wherein X is bromine or chlorine;

Process for preparation of optically active .alpha.-bromo and

A process for the asymmetric hydrogenation of a compound of the formula ##STR1## wherein each R, independently, is alkyl, arylmethyl, aryl, alkoxy, arylmethoxy or aryloxy or both R's, taken together, are methylene, ethylene or 1,2-phenylene and n is 1,2 or 3, or of a salt thereof to a compound of the formula ##STR2## in the form of an (S) or (R) enantiomer, wherein R and n have the significances given above, using an optically active ruthenium-diphosphine complex as catalyst, is described. The preparation of the compounds of formula II, as well as the compounds of formula II, which form a further object of the invention, are also described.

Asymmetric hydrogenation process using ruthenium-diphosphine complexe

The compounds of the formula ##STR1## wherein R is OH, NH.sub.2, lower-alkyl-NH or phenyl-lower alkyl-NH are presented. These compounds can be catalytically hydrogenated to the corresponding .alpha.-aminocarboxylic acid derivatives which are intermediates in the synthesis of therapeutic pseudopeptides.

Optically active iminocarboxylic acid derivatives

There is described a process for the manufacture of isoprene derivatives of the general formula ##STR1## wherein the asymmetric centres can each individually have the (R)- or (S)-configuration, R represents a residue of the formulae ##STR2## R.sup.1 signifies lower alkyl or both R.sup.1 's together signify ethylene or propylene and n stands for the number 0, 1 or 2, in which a compound, which is present in the (E)- or (Z)-form, of the general formula ##STR3## wherein R, n and an optionally present asymmetric centre have the above significance, is asymmetrically hydrogenated with a ruthenium complex of an optically active atropisomeric diphosphine.

Assymetric hydrogenation of isoprene derivatives

The present invention is concerned with a process for the manufacture of optically active compounds of the formula ##STR1## wherein R signifies lower alkyl, lower alkoxy, phenyl, benzyl or --NR.sub.2.sup.1, R.sup.1 signifies lower alkyl, phenyl, benzyl or hydrogen and * signifies an optically active center, by asymmetrically hydrogenating an enol derivative of ketoisophorone of the formula ##STR2## wherein R has the significance given above, in the presence of a rhodium complex of an optically active diphosphine ligand.

Process for the enantioselective hydrogenation of ketosiophorone

The present invention is concerned with novel optically active phosphorus compounds of the general formula ##STR1## wherein R and R.sup.1 each independently signify hydroxy, a protected hydroxy group, lower alkyl or lower alkoxy and

Optically active phosphorous compounds

A novel process for the asymmetric hydrogenation of compounds of the formula: ##STR1## wherein R represent aryl or heteroaryl, to compounds of the formula: ##STR2## wherein R has the above significance, is carried out using rhodium-diphosphine complexes.

Assymetric synthesis process

Phosphorus compounds

A catalytic process for the manufacture of optically active compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are alkyl, which is optionally interrupted by an O atom in a position other than the .alpha.-or .beta.-position, or optionally substituted benzyl,

Process for the preparation of optically active compounds

A process for the asymmetric hydrogenation of 6,7-dihydropyrido[1,2-a]indole-8-methanol or its aromatically-substituted derivatives of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 each, independently, is hydrogen, halogen, C.sub.1-7 -alkyl, C.sub.1-7 -haloalkyl, hydroxy, C.sub.1-7 -alkoxy, C.sub.1-7 -alkylthio, C.sub.1-7 -alkylsulfinyl, C.sub.1-7 -alkylsulfonyl, nitro, amino or acylamino, to (S)- or (R)-compounds of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 have the significances given above and the asterisk (*) denotes the chiral center, carried out using optically active rhodium-diphosphine complexes as catalysts, is described. The production of the compounds II, which also form an object of the invention, is also described. The compounds I and II are valuable intermediates, for example, for the preparation of pharmaceutically active substances.

Asymmetric hydrogenation of dihydro-pyrido [1,2-a]indoles

A process for the preparation of isoquinoline derivatives of the formulas ##STR1## wherein R.sup.1 and R.sup.2 have the significances herein after set forth in the description, is described. The compounds of formula IV are obtained by asymmetrically hydrogenating the compounds of formula I. The compounds of formula I are, in turn, obtained by isomerizing compounds of the formulas ##STR2## or a mixture of compounds of the formulas ##STR3##

Isoquinoline derivatives

There is disclosed a process for the asymmetrical hydrogenation of (E)-2-methyl-3-phenyl-2-propen-1-ol of formula ##STR1## wherein R.sub.1 is as defined herein, to give compounds of formula ##STR2## The catalyst is a neutral or cationic rhodium complex of a chiral atropisomeric phosphine.

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Magden, Switzerland

Emil A Broger