Process for the selective alkylation of aldehydes by means of organozinc compounds
AssigneeMetallgesellschaft Aktiengesellschaft
InventorsPaul Knochel, Christian Lutz
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Abstract
There is described a process for the enantioselective alkylation of aldehydes by means of organozinc compounds, of which a ligand of the zinc is transferred to the aldehyde, and the other ligand acts as so-called dummy ligand. As novel substances there are used zinc-organic compounds, which contain the neophyl residue as dummy ligand.
Claims12
A process for the enantioselective alkylation of aldehydes with organozinc compounds, comprising transferring a functionalized alkyl group (R-FG) to an aldehyde according to the equation I
- wherein R1 is selected from the group consisting of alkyl, aryl, functionalized alkyl and functionalized aryl,
- RDum is an organic residue selected from the group consisting of
- —CH2—C(R2, R3, R4) wherein
- R2 is selected from the group consisting of H, alkyl and aryl;
- R3 is selected from the group consisting of alkyl and aryl;
- R4 is selected from the group consisting of alkyl and aryl,
- and —CH—(CH3)(R5) wherein
- R5 is alkyl;
- (R-FG) is selected from the group consisting of alkyl and a functionalized alkyl group having a ketocarbonyl, ester, amine, carboxylic acid amide, nitrile, cyanate, isocyanate, ether, enolether, halogen, aromatic or CC multiple-bond function, wherein
- RDum≠R-FG;
- and wherein the solvent is selected from the group consisting of a 5 to 12 carbon aliphatic hydrocarbon, an aromatic hydrocarbon, an ether and a chlorinated hydrocarbon, and
- wherein * in compound IV is a chiral center of compound IV.
An alkyl-zinc compound of the formula RDum-Zn-(R-FG), wherein RDum is neophyl and (R-FG) is selected from the group consisting of alkyl and a functionalized alkyl group having a ketocarbonyl, ester, amine, carboxylic acid amide, nitrile, cyanate, isocyanate, ether, enolether, halogen, aromatic or CC multiple-bond, and wherein (R-FG) is not neophyl.
Dependencies are inferred from the claim text.