Process for the cyanation of aldehydes
AssigneeNesmey Anov Institute of Organoelement Compounds
InventorsYuri Belokon, Michael North
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Abstract
A process for cyanating an aldehyde is provided. The process comprises reacting the aldehyde with: i) a cyanide source which does not comprise a Si—CN bond or a C—(C═O)—CN moiety; and ii) a substrate susceptible to nucleophilic attack not comprising a halogen leaving group; in the presence of a chiral catalyst. Preferably, the chiral catalyst is a chiral vanadium or titanium catalyst. The cyanide source is preferably an alkali metal cyanide and the substrate susceptible to nucleophilic attack not comprising a halogen leaving group is a carboxylic anhydride.
Claims17
A process for cyanating an aldehyde which comprises reacting the aldehyde with:
- i) a cyanide source which does not comprise a Si—CN bond or a C—(C═O)—CN moiety;
- and
- ii) a substrate susceptible to nucleophilic attack not comprising a halogen leaving group;
- in the presence of a chiral catalyst.
A process according to any preceding claim, wherein the chiral catalyst comprises a complex of vanadium or titanium.
A process according to any preceding claim, wherein the process is carried out in the presence of an additive having a pKa of greater than 10.
A process according to any preceding claim, wherein the process is carried out in a polar, aprotic solvent.
A process according to any preceding claim, wherein the substrate susceptible to nucleophilic attack not comprising a halogen leaving group is added to a mixture of chiral catalyst, cyanide source, aldehyde, and optionally solvent and additive having a pKa of greater than 10.
A process for the cyanation of an aldehyde group which comprises reacting the aldehyde with:
- i) an alkali metal cyanide;
- and
- ii) a carboxylic anhydride;
- in the presence of a catalyst comprising a chiral complex of titanium or vanadium.
A process for the preparation of an O-acyl cyanohydrin which comprises reacting an aldehyde with potassium cyanide and a carboxylic anhydride in the presence of a catalyst comprising a chiral complex of titanium or vanadium.
A composition of matter comprising a mixture of a chiral transition metal catalyst and a metal cyanide.
A catalyst of formula (3a) or (3b):
- 9
- wherein,
- R7 and R8 are independently hydrogen, halogen, cyano, nitro, hydroxy, amino, thiol, an optionally substituted hydrocarbyl, perhalogenated hydrocarbyl, an optionally substituted heterocyclyl, an optionally substituted hydrocarbyloxy, an optionally substituted mono or di-hydrocarbylamino, an optionally substituted hydrocarbylthio, an optionally substituted acyl, an optionally substituted ester, an optionally substituted carbonate, an optionally substituted amide, or an optionally substituted sulphonyl or sulphonamido group, or comprise part of a fused ring;
- R9 and R10 are independently halogen, cyano, nitro, hydroxy, amino, thiol, an optionally substituted hydrocarbyl, perhalogenated hydrocarbyl, an optionally substituted heterocyclyl, an optionally substituted hydrocarbyloxy, an optionally substituted mono or di-hydrocarbylamino, an optionally substituted hydrocarbylthio, an optionally substituted acyl, an optionally substituted ester, an optionally substituted carbonate, an optionally substituted amide, or an optionally substituted sulphonyl or sulphonamido group, or R9 & R10 optionally are linked in such a way as to form an optionally substituted ring(s);
- Y1 is a neutral ligand;
- and
- X is an anion.
Dependencies are inferred from the claim text.