Process for resolution of chiral alcohols or phenols or chiral lactonic compounds
AssigneeRoussel Uclaf
InventorsJacques Martel, Jean Tessier, Andre Teche
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AssigneeRoussel Uclaf
InventorsJacques Martel, Jean Tessier, Andre Teche
Estimating the term…
Novel ethers of organic compounds containing chiral atoms of the formula ##STR1## wherein A is a hydrocarbonated chain of 1 to 10 groups, the said chain containing one or more heteroatoms, one or more unsaturations, the assembly of the groups constituting the chain may represent a mono- or polycyclic system, including a system of the spiro or endo type, the chain A can contain one or more chiral atoms or the lactone moiety can present a chirality due to the dissymmetric spatial configuration of the whole of the molecule and Z is selected from the group consisting of primary, secondary or tertiary alcohol moiety containing at least an asymmetric carbon atom, a phenol moiety substituted comprising at least one asymmetric carbon atom and a substituted alcohol or phenol moiety with a chirality due to the dissymmetric spatial configuration of the whole of the molecule, with the proviso Z is not (R) or (S) .alpha.-cyano-3-phenoxy-benzyl when A is ##STR2## which are useful for the resolution of compounds of the formulae ##STR3## wherein A and Z have the above definitions and X is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms.
A process of resolving chiral alcohols or phenols of the formula ZOH or chiral lactonic compounds of the formula ##STR18## wherein A is selected from the group consisting of bicyclic hydrocarbon chain of 5 to 10 carbon atoms optionally containing one unsaturation, radicals ##STR19## wherein Y and Y' are individually selected from the group consisting of hydrogen, fluorine, bromine, chlorine and alkyl of 2 to 6 carbon atoms or taken together with the carbon atoms to which they are attached form a carbon homocycle of 3 to 7 carbon atoms, the chain A can contain one or more chiral atoms or the lactone moiety can present a chirality due to the dissymetric spatial configuration of the whole of the molecule and Z is derived from hydroxy compound selected from the group consisting of aliphatic, cycloaliphatic, aromatic and heterocyclic primary, secondary or tertiary alcohols and a substituted phenol containing at least one asymetric carbon atom or having a chirality due to the dissymetric spatial configuration of the whole of the molecule, with the proviso Z is not (R) or (S) .alpha.-cyano-3-phenoxy-benzyl when A is ##STR20## comprising reacting a lactonic compound of the formula ##STR21## wherein A has the above definition and X is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms in the presence of an acid with a phenol or alcohol of the formula
Dependencies are inferred from the claim text.