Process for the manufacture of tertiary, optically active aliphatic compounds
AssigneeHoffmann-La Roche Inc.
InventorsRichard Barner, Walter Boguth, Hans G. W. Leuenberger, Max Schmid, Reinhard Zell
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Abstract
A process for asymmetrically hydrogenating through the use of microorganisms a double bond connected to tertiary carbon atom in an olefinic aliphatic compound to produce a tertiary, optically active aliphatic compound useful as an intermediate for optically active Vitamins E and K.
Claims24
A process for producing a tertiary optically active aliphatic compound of the formula ##STR81## wherein X' and Y' are different functional groups, one is carboxy, esterified carboxy and the other is carboxy, hydroxymethyl, esterified carboxy or etherified or esterified hydroxymethyl;
- wherein the carboxy and hydroxymethyl groups are lactonized with one another with the formation of the group --CO--O--CH.sub.2 -- or --CH.sub.2 --O--CO--, and wherein when X' is alkyl-etherified hydroxymethyl, Y' is also hydroxymethyl or esterified hydroxymethyl, comprising fermentatively hydrogenating an olefinic compound of the formula:
- ##STR82## wherein X is carboxy, esterified carboxy, hydroxymethyl etherified or esterified hydroxymethyl and Y is carboxy, formyl, hydroxymethyl, esterified carboxy, acetalized formyl or etherified or esterified hydroxymethyl;
- wherein X and Y are different functional groups;
- wherein when X is hydroxymethyl or esterified hydroxymethyl, Y is carboxy, formyl, or acetalized formyl and when Y is hydroxymethyl or esterified hydroxymethyl, X is esterified carboxy or alkyl-etherified hydroxymethyl, with an aerobic or facultative microorganism capable of hydrogenating a double bond situated in an aliphatic chain between a CH and methylated CH moiety in an aqueous medium to obtain said tertiary optically active aliphatic compound as a fermentation product.
Dependencies are inferred from the claim text.