Hoffmann-la Roche Inc.

Givaudan Corporation

Roche Vitamins Inc.

Ciba-geigy Corporation

Rolic Ag

Yvo Crameri

Emil A Broger

Michelangelo Scalone

Erich Widmer

Peter Schudel

Paul A Ochsner

Kurt P&uuml;ntener

Richard Buchecker

Albert Pfiffner

Rudolf Schmid

Ulrich Widmer

Pius Waldmeier

Teodor Lukac

Reinhard Zell

Hans G Leuenberger

Hans P Isenring

Bernd Heiser

Theodor Siegfried

Marquard Imfeld

Francedillaois Montavon

Process for the preparation of ethanesul fonyl-piperidine derivatives

Amino-amide-ruthenium complexes

A process for the manufacture of trans-(R,R)-actinol by diasteroselective transfer hydrogenation of levodione comprises hydrogenating (R)-levodione in the presence of a hydrogen donor, which simultaneously can be used as the solvent, and an amino-amide-ruthenium complex, especially of the formula RuH(L&lcub;&mdash;H&rcub;)(Y), wherein Y signifies a neutral ligand and L signifies an optionally optically active monosulphonylated diamine ligand, as defined in more detail in the description. Moreover, the invention is concerned with some of the amino-amide-ruthenium complexes and with the corresponding precursors to these complexes, which have halogen in place of H. The product of the process in accordance with the invention, trans-(R,R)-actinol, is known as an important building block for the synthesis of carotenoids, e.g. zeaxanthin. By the process trans-(R,R)-actinol is made available in particularly high enantiomeric and diasteromeric purity.

Process for the preparation of trans-(R,R)-actinol

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 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

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.

Asymmetrical hydrogenation

The present invention describes novel chiral rhodium-diphosphine complexes having the formula

Chiral rhodium-diphosphine complexes

The invention is concerned with novel isoquinoline derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen, lower alkyl, lower alkoxy, aryl, aryloxy, aryl-lower alkyl or aryl-lower alkoxy and

Isoquinoline derivatives

There are described novel chiral rhodium-diphosphine complexes of the formula

Novel chiral phosphines are disclosed which when complexed with rhodium provide catalyst compositions for asymmetric hydrogenations.

Chiral phosphines

Rhodium complexes of chiral phosphines

There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.

3-Phenyl-propionaldehydes

Process for the preparation of dihydrocinnamaldehyde derivatives

The compound 6-hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohe xen-1-one useful as intermediate for producing the natural coloring agent astaxanthin as well as a method for synthesizing astaxanthin from this compound and synthesizing the compound from 2-hydroxyketo isophorone.

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Oberwil, Switzerland

Yvo Crameri